[ CAS No. 112-80-1 ]

Name: 112-80-1|(9Z)-9-Octadecenoic acid|98%
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Quality Control of [ 112-80-1 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 112-80-1 ]

CAS No. :	112-80-1	MDL No. :	MFCD00064242
Formula :	C₁₈H₃₄O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	N/A
M.W :	282.46 g/mol	Pubchem ID :	-
Synonyms :	1. Oleic acid

Calculated chemistry of of [ 112-80-1 ]

Physicochemical Properties

Num. heavy atoms :	20
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.83
Num. rotatable bonds :	15
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	89.94
TPSA :	37.3 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	Yes
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-2.6 cm/s

Lipophilicity

Log Po/w (iLOGP) :	4.27
Log Po/w (XLOGP3) :	7.64
Log Po/w (WLOGP) :	6.11
Log Po/w (MLOGP) :	4.57
Log Po/w (SILICOS-IT) :	5.95
Consensus Log Po/w :	5.71

Druglikeness

Lipinski :	1.0
Ghose :	None
Veber :	1.0
Egan :	1.0
Muegge :	1.0
Bioavailability Score :	0.56

Water Solubility

Log S (ESOL) :	-5.41
Solubility :	0.00109 mg/ml ; 0.00000385 mol/l
Class :	Moderately soluble
Log S (Ali) :	-8.26
Solubility :	0.00000154 mg/ml ; 0.0000000055 mol/l
Class :	Poorly soluble
Log S (SILICOS-IT) :	-5.39
Solubility :	0.00114 mg/ml ; 0.00000404 mol/l
Class :	Moderately soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	2.0
Synthetic accessibility :	3.07

Safety of [ 112-80-1 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 112-80-1 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 112-80-1 ]
Downstream synthetic route of [ 112-80-1 ]

[ 112-80-1 ] Synthesis Path-Upstream 1~13

1
[ 1008-88-4 ]
[ 112-80-1 ]
[ 33421-40-8 ]
[ 87109-10-2 ]

Reference： [1] Patent: US4386209, 1983, A,

2
[ 1008-88-4 ]
[ 112-80-1 ]
[ 33421-40-8 ]
[ 87109-10-2 ]

Reference： [1] Patent: US4386209, 1983, A,

3
[ 112-80-1 ]
[ 504-40-5 ]
[ 555-43-1 ]
[ 2846-04-0 ]

Reference： [1] Chemische Berichte, 1903, vol. 36, p. 2767[2] Chem. Zentralbl., 1904, vol. 75, # II, p. 413

4
[ 112-80-1 ]
[ 627-91-8 ]
[ 1120-34-9 ]

Reference： [1] Journal of the Chemical Society, 1953, p. 2393,2397

5
[ 107-97-1 ]
[ 112-80-1 ]
[ 4316-73-8 ]
[ 110-25-8 ]

Reference： [1] Patent: US5710295, 1998, A,

6
[ 122-32-7 ]
[ 112-80-1 ]
[ 4704-94-3 ]

Reference： [1] Journal of Molecular Catalysis B: Enzymatic, 2014, vol. 102, p. 16 - 24

7
[ 112-80-1 ]
[ 3937-56-2 ]

Reference： [1] Polymer, 2011, vol. 52, # 20, p. 4503 - 4516

8
[ 112-80-1 ]
[ 4494-16-0 ]

Yield	Reaction Conditions	Operation in experiment
47%	at 45℃; for 72 h; Inert atmosphere	Compound 4 was prepared according to a literature procedure.2 Oleic acid (89 g (90percent), 0.315 mol)was transferred into a 250-mL three-necked round-bottomed flask via syringe and out gassed with N2 for 0.5 h. 1,3-Bis-(2,4,6-trimethylphenyl)-2-(imidazolidinylidene) (dichlorophenylmethylene)-tricyclohexylphosphine) ruthenium (267 mg, 0.315 mmol), 2nd generation Grubbs catalyst, was then added. The reaction mixture was stirred with a mechanical stirrer and heated at 45°C, and after ~5min the diacid began to precipitate from the reaction mixture. After 3 days stirring the crude product was quenched with ethyl vinyl ether (40 mL), and excess ether was removed under reduced pressure. The residue was recrystallized several times from a mixture of hexane (300 mL) and ethylacetate (50 mL) to give pure 4 as a white solid (23.5 g, 7.52 mmol, 47 percent). m.p. 97–98 °C. 1H NMR(300 MHz, CD3OD): δ 5.39 (m, 2H, –CH=CH–), 2.27 (t, 4H, J = 7.35 and 7.35 Hz, –CH2–COOH), 1.97 (m, 4H), 1.60 (m, 4H), 1.32 (m, 16H, –CH2–). 13C NMR (75 MHz, CD3OD): δ181.0 (s, –COOH), 131.6 (d, 2C, –CH=CH–), 35.1, 33.7, 30.8, 30.4, 30.3, 30.2, 26.2.
29.75 g	at 45℃; for 24 h; Inert atmosphere	Oleic acid (76 g) was transferred into a 250 mL three-necked round bottom flask and stirred at 45° C. under nitrogen gas for 0.5 hours. Grubbs 2^ndgeneration catalyst (85 mg) was added. The reaction mixture was stirred at 45° C. for around 5 min. The diacid began to precipitate from the reaction mixture. The reaction was kept at this temperature for 24 hours, and then quenched with ethyl vinyl ether (15 mL). The excess ether was removed under reduced pressure. The residue was purified by recrystallization from ethyl acetate and hexanes (1:2) to give 29.75 g of product as a white solid.

Reference： [1] Synthetic Communications, 2014, vol. 44, # 8, p. 1149 - 1154
[2] Patent: US2011/300590, 2011, A1, . Location in patent: Page/Page column 7
[3] Patent: US2015/321992, 2015, A1, . Location in patent: Paragraph 0050
[4] Angewandte Chemie - International Edition, 2017, vol. 56, # 26, p. 7589 - 7594[5] Angew. Chem., 2017, vol. 129, # 26, p. 7697 - 7702,6

9
[ 112-80-1 ]
[ 4494-16-0 ]
[ 5557-31-3 ]

Yield	Reaction Conditions	Operation in experiment
71%	Stage #1: at 45℃; for 24.08 - 72 h; Neat (no solvent)	Oleic acid ((3b), 89 g (90percent, 0.315 mol) was transferred into a 250 mL 3-neck round bottom flask via syringe and out-gassed with nitrogen gas for 0.5 h. 1,3-Bis-(2,4,6-trimethylphenyl)-2-(imidazolidinylidene)(dichlorophenylmethylene)(tricyclohexylphosphine)ruthenium (2, 267 mg, 0.315 mmol), a second generation Grubbs catalyst, was then added; no solvent was utilized. The reaction mixture was stirred with a mechanical stirrer and heated at 45° C. and after about 5 minutes a white precipitate formed. After 24 h reaction, about 10 mg of crude product was removed from the reaction mixture and transferred to a 2 mL dram vial. The crude diacid product (5b, eq. 1) was added to 1 mL of methanol and two drops of conc. sulfuric acid were added. The resulting mixture was heated at 80° C. for 0.5 h (Christie, W. W., Lipid analysis: Isolation, Separation, Identification, and Structural Analysis of Lipids, Oxford, N.Y. Pergamon Press (1982)). The reaction mixture was then quenched with 2 mL of 1M Na₂CO₃, extracted with diethyl ether (3.x.2 mL) and the combined ether layers washed with water (3.x.2 mL). The organic layer was dried with MgSO₄, filtered, solvent removed under reduced pressure, and the methylated diacid 5b characterized by GC/MS: (retention time=14.2 min) and gave an [M]⁺ of m/z 340 (calc., [M]⁺ for 5b is m/z=340.26). The remainder of the crude product was quenched with ethyl vinyl ether (20 mL) and excess ether was removed under reduced pressure. The residue was recrystallized from a mixture of hexane (300 mL) and ethyl acetate (50 mL) twice to give pure 1,18-octadec-9-enedioic acid (5b, eq. 1) as a white solid, m. p., 97.5-98.5° C. (lit. m. p., 88° C. (Van Dam, P. B., et al., J. Am. Oil. Chem. Soc., 51: 389-391 (1974)). Isolated yield: 35 g (71percent). ¹H NMR of 1,18-octadec-9-enedioic acid (CD₃OD, 400 MHz): δ 5.39 (m, -CHCH-, 2H), 2.28 (t, J=7.2 Hz _{7.6 Hz, -CH&2}CO₂H, 4H), 1.98 (m, 4H), 1.60 (m, 4H), 1.32 (m, 16H). ¹³C NMR (CD₃OD, 100 MHz): δ 177.8 (s, CO₂H), 131.6 (s, CHCH), 35.1 (s), 33.7 (s), 30.8 (s), 30.4 (s), 30.3 (s), 30.2 (s), 26.2 (s).

Reference： [1] JAOCS, Journal of the American Oil Chemists' Society, 2006, vol. 83, # 7, p. 629 - 634
[2] Patent: US7534917, 2009, B1, . Location in patent: Page/Page column Sheet 2/6; 6-8; 16; 18
[3] Patent: EP1251135, 2002, A2, . Location in patent: Page 16
[4] Journal of the American Chemical Society, 2012, vol. 134, # 33, p. 13716 - 13729

10
[ 112-80-1 ]
[ 74-85-1 ]
[ 4494-16-0 ]
[ 14436-32-9 ]

Reference： [1] Patent: US2015/336871, 2015, A1, . Location in patent: Paragraph 0071-0081

11
[ 6117-80-2 ]
[ 112-80-1 ]
[ 4494-16-0 ]
[ 75039-83-7 ]
[ 79868-94-3 ]
[ 5557-31-3 ]

Reference： [1] Beilstein Journal of Organic Chemistry, 2011, vol. 7, p. 1 - 8

12
[ 25260-60-0 ]
[ 112-80-1 ]
[ 4494-16-0 ]
[ 101171-21-5 ]
[ 68480-27-3 ]
[ 5557-31-3 ]

Reference： [1] Beilstein Journal of Organic Chemistry, 2011, vol. 7, p. 1 - 8

13
[ 112-80-1 ]
[ 74-85-1 ]
[ 4494-16-0 ]
[ 872-05-9 ]
[ 14436-32-9 ]
[ 5557-31-3 ]

Reference： [1] Patent: EP1251135, 2002, A2, . Location in patent: Page 16-17

[ 112-80-1 ] Synthesis Path-Downstream 1~32

1
[ 112-80-1 ]
[ 623-69-8 ]
oleic acid-(β,β'-dimethoxy-isopropyl ester) [ No CAS ]

Reference： [1],1947,vol. 24,p. 163,164
Chem.Abstr.,1947,p. 1136

2
[ 112-80-1 ]
[ 504-40-5 ]
[ 555-43-1 ]
[ 2846-04-0 ]

Reference： [1]Chemische Berichte,1903,vol. 36,p. 2767
Chemisches Zentralblatt,1904,vol. 75,p. 413

5
[ 107-97-1 ]
[ 112-80-1 ]
[ 4316-73-8 ]
[ 110-25-8 ]

Yield	Reaction Conditions	Operation in experiment
	In water; isopropyl alcohol;	EXAMPLE 2 A reactor equipped with a mechanical stirrer, heating mantle, thermometer, and a nitrogen atmosphere, was charged with 35.04 g (0.125 mole) of oleic acid. The oleic acid was heated to 80 C. and 13.8 g (0.125 mole) of solid <strong>[4316-73-8]sodium sarcosinate</strong> was added. This mixture was heated to 170 C. with a constant nitrogen sparge. When the reaction mixture reached 170 C., 11.4 g (0.125 mole) of solid <strong>[4316-73-8]sarcosine</strong> acid was added. The reaction mixture was sampled after ten hours at 170 C. and the conversion based on oleic acid was 84.2%. The crude reaction mixture was dissolved in 60 g of a 50/50 volume ratio of isopropanol and water. This solution was acidified with sulfuric acid to a pH of 1. Upon acidification, the solution formed two layers. The upper layer, containing the product, was separated and concentrated resulting in N-oleoyl <strong>[4316-73-8]sarcosine</strong>.

Reference： [1]Patent: US5710295,1998,A

6
[ 112-80-1 ]
[ 623-57-4 ]
[ 127512-29-2 ]

Yield	Reaction Conditions	Operation in experiment
88.9%		2.41 kg of Nu,Nu'-carbonyldiimidazole is dissolved at room temperature in 6.33 kg of dry acetonitrile. The resultant solution is heated to 25°C. Then 4.0 kg of oleic acid is pumped into the solution over a period of 60 minutes while the reaction temperature is regulated below 35°C by the variation of the addition speed (formation of carbon dioxide gas). After the addition is completed the reaction solution is stirred for additional 90 minutes at 30°C (gas evolution ended). Then 11 g of 1 ,8-diazabicyclo[5.4.0]undec-7-ene is added followed by a solution of 0.83 kg of racemic (R,S)-3-(dimethylamino)- 1 ,2-propanediol in 0.37 kg of dry acetonitrile. Stirring at 30°C is continued for 21 hours. The resultant emulsion is cooled to 25°C and stirring is stopped. Two layers appear. The lower layer is isolated, degassed at 1 mbar/25°C for 200 minutes and finally diluted with 11.7 kg n-heptane. To the solution is added 1.21 kg of basic aluminium oxide and the suspension is stirred for 3 hours at 0°C. The suspension is filtered and the filter residue is washed with 1.5 kg of n-heptane previously cooled down to 0°C. The combined filtrates are homogenized to yield 15.9 kg solution of 4.08 kg pure (2R,S)-DODAP in n-heptane (lot no. MBA-116, assay: 25.7percent, yield:88.9percent).
11.12 g	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In chloroform; at 20 - 30℃; for 1h;	<strong>[623-57-4]3-(dimethylamino)-1,2-propanediol</strong> 2.00 g (16.78 mmol, manufactured by Tokyo Chemical Industry Co., Ltd.), Oleic acid 9.48 g (33.56 mmol, Nisshin Oil Co., Ltd. "EXTRA OLEIN 99"), 4-dimethylaminopyridine 0.41 g (3.36 mmol, product of Koei Chemical Industry Co., Ltd.) was dissolved in 120 g of chloroform. There, 1-ethyl-3- (3-dimethylaminopropyl) carbodiimide hydrochloride 7.72 g (40.27 mmol, product of Tokyo Chemical Industry Co., Ltd.) And the mixture was stirred at 20 to 30 ° C. After 1 hour, it was washed with 120 g of ion exchange water and 120 g of 25 wtpercent saline, and 3.0 g of anhydrous magnesium sulfate was added to the organic layer and stirred. The magnesium sulfate was filtered off, The filtrate was desolvated with an evaporator to obtain DODAP (yield: 11.12 g, 17.16 mmol).

Reference： [1]Chemical Communications,2012,vol. 48,p. 5575 - 5577
[2]Patent: WO2012/159704,2012,A1 .Location in patent: Page/Page column 15
[3]Chemistry and Physics of Lipids,2000,vol. 105,p. 189 - 191
[4]Chemical Communications,2011,vol. 47,p. 12613 - 12615
[5]Patent: JP2016/108343,2016,A .Location in patent: Paragraph 0051

7
[ 112-80-1 ]
[ 28319-77-9 ]
[ 4235-95-4 ]

Reference： [1]Chemistry and Physics of Lipids,2005,vol. 137,p. 94 - 99

8
[ 112-80-1 ]
[ 1453-93-6 ]
(Z)-Octadec-9-enoic acid (3S,5R,6S,8R,9R,10R,12R,13R,14R,17S)-6,12-dihydroxy-17-((S)-1-hydroxy-1,5-dimethyl-hex-4-enyl)-4,4,8,10,14-pentamethyl-hexadecahydro-cyclopenta[a]phenanthren-3-yl ester [ No CAS ]

Reference： [1]Biological and pharmaceutical bulletin,2002,vol. 25,p. 861 - 866

9
[ 112-80-1 ]
[ 1732-09-8 ]

Reference： [1]Justus Liebigs Annalen der Chemie,1838,vol. 28,p. 256

10
[ 112-80-1 ]
platinum [ No CAS ]
[ 505-54-4 ]

Reference： [1]Bulletin de la Societe Chimique de France,1961,p. 218 - 222

11
[ 3198-49-0 ]
[ 112-80-1 ]
[ 124285-49-0 ]

Yield	Reaction Conditions	Operation in experiment
90%	lipase;	EXAMPLE 5 Preparation of ethyl 6-O-(cis-9-octadecenoyl)-D-glucopyranoside The title compound was obtained as a crude product (1305 g, 90% monoester, 5% <strong>[3198-49-0]ethyl D-glucopyranoside</strong>, 5% diesters) according to example 1 using <strong>[3198-49-0]ethyl D-glucopyranoside</strong> (606 g, 2.9 mol), cis-9-octadecenoic acid (1111 g, 3.9 mol) and immobilized lipase (30.5 g). The reaction was complete in 48 hours.

Reference： [1]Patent: US5191071,1993,A

12
[ 31608-22-7 ]
[ 112-80-1 ]
[ 145437-64-5 ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate; In tetrahydrofuran;	A (Z)-9-octadecenoic acid 4-hydroxybutyl ester To a stirring solution of 2.0 g (7.0 mmol) of oleic acid and 1.6 g (7.0 mmol) of 2-(4-bromobutoxy)tetrahydro-2H-pyran in 20 mL of tetrahydrofuran is added 2.3 g (7.1 mmol) of cesium carbonate and the reaction mixture is stirred overnight at room temperature. The reaction mixture is poured into water and extracted with three 100 mL portions of ether. The combined organic layers are dried over MgSO4 and concentrated in vacuo affording 2.9 g (100%) of (Z)-9-octadecenoic acid 4-[(tetrahydro-2H-pyran-2-yl)oxy]butyl ester.

Reference： [1]Patent: US5242945,1993,A

13
aqueous sodium chloride [ No CAS ]
[ 79-37-8 ]
[ 112-80-1 ]
[ 623-57-4 ]
rac-1,2-dioleoyl-3-N,N-dimethylaminopropane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
0.92 g (84%)	With pyridine; In methanol; diethyl ether; hexane; water; benzene;	A. Synthesis of +-1,2-dioleoyl-3-N,N-dimethylamino-propane (AL-1). This compound was prepared by the method of Leventis et al. (Biochim. Biophys. Acta 1029:124-132, 1990). Three ml (35 mmol) of oxalyl chloride was added to 1.0 g (3.5 mmol) oleic acid dissolved in 10 ml benzene and stirred at room temperature for 1 h. After removal of solvent and excess oxalyl chloride under vacuum, the acid chloride was dissolved in 5 ml diethyl ether, and a further 5 ml of ether containing 0.20 g (1.7 mmol) of 3-N,N-dimethylamino-1,2-propanediol and 0.15 g pyridine was added. The resulting mixture was stirred at room temperature for 30 minutes before quenching with 1 ml methanol and removing solvents under vacuum. The crude product was dissolved in 50 ml hexane and washed with 2*25 ml 0.1M potassium hydroxide in methanol/water (1:1) followed by 25 ml 0.1M aqueous sodium chloride. Drying over anhydrous sodium sulphate and removal of hexane under vacuum gave a slightly yellow oil. Column chromatography on silica gel (70-230 mesh), eluding with ethyl acetate, gave 0.92 g (84percent) of pure product (TLC, Rf =0.5).

Reference： [1]Patent: US5595756,1997,A

14
[ 112-80-1 ]
[ 7768-28-7 ]
[ 1037077-56-7 ]

Reference： [1]Journal of Agricultural and Food Chemistry,2008,vol. 56,p. 5083 - 5090

15
[ 112-80-1 ]
[ 136236-51-6 ]
[ 1260684-14-7 ]

Yield	Reaction Conditions	Operation in experiment
94%	In di-isopropyl ether; for 1.5h;Inert atmosphere;Product distribution / selectivity;	To a solution of 4.5 g (26.3 mmol) <strong>[136236-51-6]rasagiline</strong> in 120 ml diisopropyl ether 8.3 ml (26.3 mmol, 1.0 eq) oleic acid was added under nitrogen. After stirring for 90 min, the solvent was removed in vacuo at 300C. Drying on the rotary evaporator was continued for another 2 h at this temperature. Drying in high vacuum for 2 h yielded 11.2 g (24.7 mmol, 94 %) of a yellow oil.1H NMR (de-DMSO, 300 MHz): delta = 7.31 (m, 1 H, PhH), 7.21-7.10 (m, 3 H, PhH), 5.30 (t, J = 4.8 Hz, 2 H, olefin-H), 4.25 (t, J = 6.3 Hz, 1 H, N-CH), 3.37 (d, J = 2.8 Hz, 2 H, N-CH2), 3.04 (t, J = 2.4 Hz, 1 H, alkynyl-H), 2.90 (m, 1 H, ring-CH), 2.71 (quint, J = 15.0, 7.5 Hz, 1 H, ring-CH), 2.26 (m, 1 H, ring-CH), 2.15 (t, J = 7.5 Hz, 2 H, C(O)CH2), 1.97 (m, 4 H, 2 x C=CHCH2), 1.76 (m, 1 H, ring-CH), 1.48 (brt, J = 7.2 Hz, 2 H, C(O)CH2CH2), 1.25-1.21 (s, 18 H, 9 x CH2), 0.84 (t, J = 6.3 Hz, 3 H, omega-CH3). The integrals show a ratio of amine/acid = 1 :1.IR: v = 2925.56, 2854.04, 1712.92, 1615.04, 1551.28, 1459.31 , 1402.52 cm"1. IR indicates protonation of the amine.HPLC (by area%): 99.80 %.

Reference： [1]Patent: WO2011/3938,2011,A1 .Location in patent: Page/Page column 14-15

16
[ 112-80-1 ]
[ 623-57-4 ]
[ 1352945-51-7 ]

Reference： [1]Chemical Communications,2011,vol. 47,p. 12613 - 12615

17
[ 112-80-1 ]
[ 137618-48-5 ]
C₄₄H₈₁NO₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
33.3%		General procedure: To the solution of oleic acid (3.75 g, 13.2 mmol) and 4-dimethylaminopyridine(DMAP) (270 mg) in CH2Cl2 at 0 C,N,N0-Dicyclohexylcarbodiimide (DCC) (2.75 g, 13.3 mmol) inCH2Cl2 were added dropwise. After 30 min, compound 3a (or 5a,or 6a) (11 mmol) was added, then the mixture was left for stirringat room temperature overnight. The reacting solution was cooledto 0 C, and the formed precipitate was filtered off. The filtratewas evaporated to give the residue, which was purified by silicagel column chromatography (PE/EA = 3/1, v/v) to give compound3b (or 5b, 6b).
	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 20℃; for 24h;Inert atmosphere;	Oleic acid (10mmol) was dissolved in 20ml of 12 dichloromethane, then 13 N-Boc-3-amino-glycerine (3.3mmol), 14 EDC (3mmol) and 15 DMAP (3mmol) were added. The reaction mixture was stirred at room temperature for 24h under nitrogen. After reaction, the obtained 16 Boc protected 1,2-dioleoyl-3-amino-propane (DOAP) was isolated and purified by silica column chromatography (petroleum ether/ethyl acetate 20:1).

Reference： [1]Chemistry and Physics of Lipids,2012,vol. 165,p. 809 - 817
[2]Bioorganic and Medicinal Chemistry,2015,vol. 23,p. 5756 - 5763
[3]Journal of Controlled Release,2018,vol. 279,p. 53 - 68
[4]Patent: US10426745,2019,B2 .Location in patent: Page/Page column 35; 36

18
[ 112-80-1 ]
[ 112-05-0 ]
[ 3788-56-5 ]

Reference： [1]Angewandte Chemie - International Edition,2013,vol. 52,p. 2534 - 2537
Angew. Chem.,2013,vol. 125,p. 2594 - 2597,4

19
[ 112-80-1 ]
[ 1477-68-5 ]
3'-O-methyl-N-oleoyl-dopamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
92%	With triethanolamine; benzotriazole-1-yl-oxy-tris-(dimethylamino)-phosphonium hexafluorophosphate; In tetrahydrofuran; at 20℃; for 15.25h;	Example V Synthesis of 3'-O-methyl-N-oleoyl-dopamine (Method I) 0.462 g (2.27 mmol) of 3-O-methyldopamine hydrochloride, 0.641 g (2.27 mmol) of oleic acid, 1.000 g (2.27 mmol) of BOP (Benzotriazol-1-yloxytris(dimethylamino)-phosphonium hexafluorophosphate) and 20 ml of THF were introduced into a flask. The reaction mixture was cooled down to a temperature of 0-5 C. and 0.949 ml (6.810 mmol) of triethanolamine in 4 ml THF were added drop-wise within 15 min and the reaction mixture was continuously stirred for 15 hours at room temperature. After evaporating the solvent, 100 ml of diethyl ether were added and the ether phase was washed three times with 30 ml of a 4% HCl solution, two times with 30 ml of a saturated NaHCO3 solution and two times with a saturated NaCl solution. After drying over anhydrous MgSO4 and removal of the solvent, the crude product was purified by crystallization from diethyl ether/hexane. 0.90 g (2.09 mmol) of the amide in the form of a white solid was obtained giving the reaction yield of 92%. Melting point: 78-79 C. NMR: 1H NMR: d 6.80 (d, J=7.5 Hz, 1H-5'), 6.69-6.65 (m, 2H-2', 6'), 5.70 (s, 1H-NH), 5.50 (s, 1H-OH), 5.38-5.30 (m, 2H-9.10), 3.87 (s, 3H-OCH3), 3.48 (q, J=6.0 Hz, 2H-1"), 2.74 (t, J=7.0 Hz, 2H-2"), 2.12 (t, J=8.0 Hz, 2H-2), 2.02-1.98 (m, 4H-8, 11), 1.60-1.57 (m, 2H-3), 1.32-1.26 (m, 20H-4, 5, 6, 7, 12, 13, 14, 15, 16, 17), 0.88 (t, J=7.0 Hz, 3H-18). 13C NMR: d 173.17, 146.67, 144.29, 130.67, 130.01, 129.74, 121.31, 114.42, 111.16, 55.89, 40.69, 36.87, 35.39, 31.91, 29.77, 29.72, 29.53, 29.33, 29.28, 29.27, 29.14, 27.23, 27.18, 25.78, 22.69, 14.13; Mass spectrometry: m/z=432.6 [M+H]+, 454.6 [M+Na]+;

Reference： [1]Patent: US2013/131361,2013,A1 .Location in patent: Paragraph 0050; 0051; 0052

20
[ 112-80-1 ]
[ 1453-93-6 ]
(Z)-Octadec-9-enoic acid (3S,5R,6S,8R,9R,10R,12R,13R,14R,17S)-6,12-dihydroxy-17-((S)-1-hydroxy-1,5-dimethyl-hex-4-enyl)-4,4,8,10,14-pentamethyl-hexadecahydro-cyclopenta[a]phenanthren-3-yl ester [ No CAS ]
[ 1443292-69-0 ]

Yield	Reaction Conditions	Operation in experiment
20%; 14%	With dmap; dicyclohexyl-carbodiimide; In tetrahydrofuran; at 4 - 20℃; for 24.0h;	General procedure: PPT (500 mg) and different fatty acids (butyric acid, n-pentanoic acid, hexanoic acid, heptanoic acid, octanoic acid, nonanoic acid, capric acid, lauric acid, oleic acid, 8 mmol respectively) were dissolved in 25 mL dry tetrahydrofuran. N,N?-dicyclohexylcarbodiimide (DCC, 8 mmol) and 4-dimethylaminopyridine (DMAP, 0.8 mmol) were added while cooling on ice (4C). The mixture was stirred at room temperaturefor 24h, then was filtered, washed with CHCl3 three times and the filtrate combined. The filtrate was was evaporated to dryness under 80C to obtain the crude product. The crude product was subjected to silica gel column (3cm×40cm) chromatography, eluted with a gradient of petroleum and acetone (10:1-1.1) to obtain other compounds respectively.

Reference： [1]Letters in drug design and discovery,2013,vol. 10,p. 402 - 409

21
[ 85721-33-1 ]
[ 112-80-1 ]
[ 638-68-6 ]
[ 3910-35-8 ]
heptyl octyl phthalate [ No CAS ]
3-methyl-2-propionylbenzoic acid [ No CAS ]
3-(2-hydroxy-2-methylpropyl)cyclohex-2-enone [ No CAS ]
[ 68-12-2 ]
[ 108-90-7 ]

Yield	Reaction Conditions	Operation in experiment
	With dipotassium peroxodisulfate; sulfuric acid; sodium hydroxide; In water; at 25℃; for 0.333333h;pH 5.0;UV-irradiation;Catalytic behavior; Kinetics;	The experimental set-up for the photocatalytic degradation ofCIP by immobilized TiO2nanoparticles on MMT is schematicallyFig. 2. Schematic representation of the reactor used for different processes.shown in Fig. 2. Photocatalysis of CIP was performed in a batchphotoreactor with a 500 mL working volume. A 16 W UV-A, UV-B or UV-C lamp (Sylvania, Japan) was applied as the light source.Batch studies were performed to evaluate the effect of CIP concen-tration, TiO2/MMT dose, the initial pH, UV light region, differentscavengers and enhancers on degradation efficiency. For each pho-tocatalytic experiment, 500 mL of an aqueous solution containingCIP in the range of 5-25 mg L-1with 0.025-0.150 g L-1of theTiO2/MMT nanocomposite was added in the reaction vessel. TheUV-A, UV-B or UV-C lamp was turned on at the beginning of eachexperiment. The pH of the solution was set to the desired valuewith H2SO4and NaOH (1 M). The solution pH was regulated witha Mettler Toledo pH meter (China). 5 mL samples were taken fromthe reactor at different intervals and residuals concentration of CIPwas measured using Varian Cary 100 UV-vis spectrophotometer(Australia) at the maximum wavelength of 276 nm. Degradationefficiency (%) = [(C0-Ct)/C0] × 100 was used to determine the degra-dation of CIP, where C0was the initial concentration of CIP solutionand Ctwas its concentration after a certain time (t). Adsorptionexperiments were conducted using the method applied for photo-catalytic degradation experiment without UV radiation. The zeropoint of charge (pHzpc) of the TiO2/MMT nanocomposite was mea-sured using the method described by Bessekhouad et al. with somemodifications [28]. In this approach, 500 mL 0.01 M NaCl was pre-pared and divided into five solutions with the pH ranging from 3to 10. A two hundred milligram catalyst was added to each solu-tion. Finally, the final pH of each solution was measured after 48 hshaking and plotted against the initial pH to determine the pHzpcof the catalyst. Electrophoretic mobility and the surface charge ofthe samples were carried out with the relation of the zeta poten-tial measurements. Zeta potentials of the samples were measuredusing a Zeta Meter 3.0+ (Zeta-Meter, Inc., USA). The zeta potentialof pure MMT, TiO2and TiO2/MMT was obtained to be -30.7, +21.06and -16.4 mV, respectively.

Reference： [1]Journal of Molecular Catalysis A: Chemical,2015,vol. 409,p. 149 - 161

22
[ 112-80-1 ]
[ 125414-41-7 ]
C₄₄H₈₁NO₆ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
59.7%		General procedure: To the solution of oleic acid (3.75 g, 13.2 mmol) and 4-dimethylaminopyridine(DMAP) (270 mg) in CH2Cl2 at 0 C,N,N0-Dicyclohexylcarbodiimide (DCC) (2.75 g, 13.3 mmol) inCH2Cl2 were added dropwise. After 30 min, compound 3a (or 5a,or 6a) (11 mmol) was added, then the mixture was left for stirringat room temperature overnight. The reacting solution was cooledto 0 C, and the formed precipitate was filtered off. The filtratewas evaporated to give the residue, which was purified by silicagel column chromatography (PE/EA = 3/1, v/v) to give compound3b (or 5b, 6b).

Reference： [1]Bioorganic and Medicinal Chemistry,2015,vol. 23,p. 5756 - 5763

23
[ 112-90-3 ]
[ 112-80-1 ]
[ 125238-99-5 ]
[ 207857-15-6 ]
N-(4-guanidino-1-oxo-1-(octadecylamino)butan-2-yl)octadec-9-enamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
3.2 g		Example 20 Preparation of C18(oleic)-norArg-C18 N-(4-guanidino-1-oxo-1-(octadecylamino)butan-2-yl)octadec-9-enamide (0607) Fmoc-Dab(Boc)-resin. To 5 g of 2-chlorotrityl chloride resin with 1.3 mmol/g substitution (Novabiochem, 01-64-0114) in 50 ml of dry DCM in 60 ml reaction vessel for solid phase synthesis, 5.726 g (13 mmol, 2 eq) of Fmoc-Dab(Boc)-OH (Mw=440.5, (Fmoc-(N-gamma-Boc)-L-alpha,gamma-diaminobutyric acid, AnaSpec, 28246) and 2.26 ml (13 mmol, 2.0 eq) of DIPEA (Aldrich, Mw=129.2, d=0.74) were added. (0608) Dab(Boc)-resin. After 3 hrs the resin was washed 3× with DCM/MeOH/DIPEA (17:2:1), 3×DCM, 2×DMF, 3×DCM and Fmoc group was deprotected with 50 ml of 20percent piperidine/DMF twice for 15 min. (0609) C18:1-Dab(Boc)-resin. After Fmoc deprotection the resin was washed with 3×DCM, 2×MeOH and 3×DCM and for the coupling reaction 3.7 g (13 mmol) of oleic acid (Sigma, Mw=282.47, d=0.891), 5.37 g (13 mmol) of HCTU (Mw=413.7) and 2.62 ml (13 mmol) of DIPEA (Mw=129.2, d=0.74) in 50 ml of DMF were added. (0610) After 1 hr of reaction the resin was washed with 3×DCM, 2×MeOH and 3×DCM and progress of reaction was checked by Kaiser test which was negative (no free amine groups present). (0611) C18:1-Dab(Boc)-OH (Mw=566.56) was cleaved from the resin by 1percent TFA/DCM (5×50 ml for 2 min was filtered to flask with 2 ml 10percent pyridine/MeOH) and solvent was evaporated. (0612) C18:1-Dab(Boc)-C18:1 (Mw=734.95). Second coupling was carried out in solution. To the oily residue from the previous reaction, 3.725 g (9.75 mmol) of oleyl amine (Sigma, Mw=267.49, 70percent), 4.033 g (9.75 mmol) of HCTU (Mw=413.7) and 1.69 ml (9.75 mmol) of DIPEA (Mw=129.2, d=0.74) in 50 ml of DMF were added. After 4 hr 100 ml of AcOEt was added and organic layer was washed in separatory funnel with 3×0.5 M HCl, 3×10percent NaCO3 and 3×NaCl. AcOEt layer was dried with anhydrous MgSO4 and evaporated. (0613) C18:1-Dab-C18 (Mw=635.9). To the oily residue from the previous reaction, 100 ml of 80percent TFA/DCM 2.5percent TIS was added and after 20 min solvent was evaporated. (0614) C18:1-norArg(diBoc)-C18:1 (Mw=874.13). The residue was dissolved in 50 ml of DCM and pH was adjusted to 9 with TEA. 2.348 g (6 mM, 1 eq) of 1,3-Di-Boc-2-(trifluoromethylsulfonyl)guanidine (Mw=391.36, Aldrich 15033) was added and after 4 hrs DCM was evaporated. (0615) C18:1-norArg-C18:1 (Mw=674.1) To the oily residue from the previous reaction 100 ml of 95percent TFA/DCM 2.5percent TIS was added and after 3 hrs solvent was evaporated. Crude product was purified on TELEDYNE Isco CombiFlash Rf instrument using 48 g normal phase silica gel column, 100percent DCM for 3 CV (column volume) and 0-20percent MeOH for 10 CV, detection 214 nm, flow 45 ml/min. DCM/MeOH was evaporated and residue was precipitated by 0.1M HCl. Yield: 3.2 g.

Reference： [1]Patent: US9339461,2016,B2 .Location in patent: Page/Page column 86-87

24
[ 112-80-1 ]
[ 169555-95-7 ]
C₂₆H₄₂N₂O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Example 23 Preparation of C18oleic-[4-Pal]-C16 N-(1-oxo-3-(pyridin-4-yl)-1-(hexadecylamino)propan-2-yl)octadec-9-enamide (0630) Fmoc-4-Pal-resin. To 5 g of 2-chlorotrityl chloride resin with 1.3 mmol/g substitution (Novabiochem, 01-64-0114) in 50 ml of dry DCM in 50 ml reaction vessel for solid phase synthesis 3.787 g (9.75 mmol, 1.5 eq) of Fmoc-4-Pal-OH (Mw=388.42, Advanced ChemTech) and 1.7 ml (9.75 mmol, 1.5 eq) of DIPEA (Aldrich, Mw=129.2, d=0.74) were added. (0631) 4-Pal-resin. After 2 hrs the resin was washed 3× with DCM/MeOH/DIPEA (17:2:1), 3×DCM, 2×DMF, 3×DCM and Fmoc group was deprotected with 40 ml of 20% piperidine/DMF 2 times for 15 min. (0632) C18oleic-4-Pal-resin. After Fmoc deprotection the resin was washed with 3×DCM, 2×MeOH and 3×DCM and for the coupling reaction 3.7 g (13 mmol) of oleic acid (Sigma, Mw=282.47, d=0.891), 5.37 g (13 mmol) of HCTU (Mw=413.7) and 2.62 ml (13 mmol) of DIPEA (Mw=129.2, d=0.74) in 50 ml of DMF were added. (0633) After 2 hr of reaction the resin was washed with 3×DCM, 2×MeOH and 3×DCM and progress of reaction was checked by Kaiser test which was negative (no free amine groups present). (0634) C18oleic-4-Pal-OH (Mw=430.62) was cleaved from the resin by 1% TFA/DCM (5×50 ml for 2 min was filtered to flask with 2 ml 10% pyridine/MeOH) and solvent was evaporated. (0635) C18oleic-4-Pal-C16 (Mw=654.06). Second coupling was carried out in solution. To the oily residue from the previous reaction, 2.354 g (9.75 mmol) of C16-amine (Sigma, Mw=241.46), 4.033 g (9.75 mmol) of HCTU (Mw=413.7) and 1.69 ml (9.75 mmol) of DIPEA (Mw=129.2, d=0.74) in 50 ml of DMF were added. After 4 hr 100 ml of AcOEt was added and organic layer was washed in reparatory funnel with 3×0.5 M HCl, 3×10% NaCO3 and 3×NaCl. AcOEt layer was dried with anhydrous MgSO4 and evaporated. Crude product was purified on TELEDYNE Isco CombiFlash Rf instrument using 48 g normal phase silica gel column, 100% DCM for 3 CV (column volume) and 0-20% MeOH for 10 CV, detection 214 nm, flow 45 ml/min. DCM/MeOH was evaporated and residue was precipitated by 0.1M HCl. Yield: 0.75 g.

Reference： [1]Patent: US9339461,2016,B2 .Location in patent: Page/Page column 88-89

25
[ 112-80-1 ]
[ 162558-25-0 ]
[ 609820-09-9 ]

Yield	Reaction Conditions	Operation in experiment
		Boc-DAP(N,N-diMe)-OH was preactivated with 3-(Diethoxyphosphoryloxy)-1, 2, 3-benzotriazin-4(3H)-one (DEPBT) and 2 eq of DIPEA in THF/DCM solvent mixture for 10 minutes followed by addition of linoleyl amine and subsequent stirring for 30 minutes. Crude compound was purified twice by flash chromatography: 1) normal phase silica gel (DCM/MeOH gradient) and 2) amine capped silica gel (Hexane/AcOEt gradient). The pure monoalkylated intermediate was dissolved in 1M HCl/ethyl acetate solution and the Boc group was removed within one hour followed by removal of the solvent under reduced pressure. The second alkyl chain was attached by preactivating the free carboxyl group of linoleic acid with (1-Ethyl-3-(3-dimethyllaminopropyl)-carbodiimide hydrochloride) (EDC) and N-Hydroxybenzotriazole (HOBt) in a 1:1 mixture of DMF and DCM for 10 minutes followed by addition of monoalkylated diMeDAP dissolved in DCM (pH adjusted to 6 with DIPEA) and subsequent stirring for 30 minutes. Crude compound was purified by flash chromatography (Hexane/AcOEt gradient) and converted to hydrochloride salt by stirring with 1M HCl/AcOEt. Final product was lyophilized.

Reference： [1]Patent: US2017/216227,2017,A1 .Location in patent: Paragraph 0320

26
[ 112-90-3 ]
[ 112-80-1 ]
[ 125238-99-5 ]
[ 207857-15-6 ]
N-(4-guanidino-1-((Z)-octadec-9-en-1-ylamino)-1-oxobutan-2-yl)oleamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		C18:1-norArg-C18:1 was synthesized as follows. Fmoc-N gamma-Boc-L-2,3-diaminobutyric acid was dissolved in dichloromethane (DCM), 2eq of diisopropylethyl amine (DIPEA) and the resulting solution was added to 2-chlorotrityl choride resin. After one hour, the resin was washed with DCM and Fmoc group was removed by treatment with 20percent piperidine in DMF yielding the free alpha-amine. Oleic acid was preactivated with 2-(6-Chloro-1H-benzotriazole-1-yl)-1,1,3,3-tetramethylaminium hexafluorophosphate (HCTU) and 2 equivalents of DIPEA and added to the resin and the reaction was deemed complete by negative Kaiser test. The lipidated compound was cleaved from the resin by multiple treatments with 1percent trifluoroacetic acid (TFA) in dichloromethane followed by evaporation under reduced pressure yielding free carboxylate intermediate. The second alkyl chain was attached by preactivating the free carboxyl group with (1-Ethyl-3-(3-dimethyllaminopropyl)-carbodiimide hydrochloride) (EDC) and N-Hydroxybenzotriazole (HOBt) in a 1:1 mixture of DMF and DCM for 10 minutes followed by addition of oleyl amine in same solvent and subsequent stirring for 30 minutes. Crude compound was purified by flash chromatography (Hexane/AcOEt gradient). The pure dialkylated intermediate was dissolved in 1M HCl/ethyl acetate solution and the Boc group was removed within one hour followed by removal of the solvent under reduced pressure. The resulting white solid was taken up in DCM to which was added TEA facilitate dissolution followed by treatment with 1, 3 Di-Boc-2-(trifluoromethylsulfonyl) guanidine for one hour. Upon completion of the reaction DCM was washed with 2 M sodium bisulfate, saturated sodium bicarbonate and dried over MgSO4 and removed under reduced pressure. The resulting residue was dissolved in absolute ethanol and two Boc groups were removed by adding dissolved compound drop wise to 12N HCl. Final product precipitated during reaction and was crystallized from EtOH.

Reference： [1]Patent: US2017/216227,2017,A1 .Location in patent: Paragraph 0339

27
[ 112-80-1 ]
[ 418759-58-7 ]
4-acetyl-2-methoxy-5-nitrophenyl oleate [ No CAS ]

Reference： [1]Macromolecular Bioscience,2017,vol. 17

28
[ 112-80-1 ]
[ 13515-95-2 ]
bis-oleic acid lysine methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
90.18%		(2) Oleic acid (7.6 g, 27.04 mmol) was dissolved in 60 mL of anhydrous dichloromethane.Add HOBT (3.82g, 28.32mmol),EDCI (5.44g, 28.32mmol)And DIEA (5.3g, 41.20mmol),Ar protection is stirred for one hour,Add L-lysine methyl ester hydrochloride (3.1 g, 13.31 mmol),Ar was stirred to react for 12 hours.Dry the solvent,Dissolved in 60 mL of ethyl acetate,Then use saturated sodium bicarbonate solution (60mL × 2),Saturated sodium dihydrogen phosphate solution (60mL × 2),Wash with saturated sodium chloride solution (60 mL),Dry over anhydrous magnesium sulfate for one hour.8.27 g of a pale yellow solid concentrated under reduced pressure.The yield was 90.18%.
	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; for 24.5h;Inert atmosphere; Cooling with ice;	Weigh accurately 5.0 g of H-Lys-OMe · 2HCl, 16.5 g of EDC · HCl and 6.4 g of HOBT in a 250 mL round-bottomed flask with a tube, evacuated, Charge nitrogen and add 30 mL of DCM to dissolve. Then 15.7 mL of oleic acid was added, Add 35.4 mL of DIEA for 0.5 h under ice bath, Then reacted at room temperature for 24 h. Oil pump to remove the solvent by rotary evaporation, The chloroform was dissolved, washed successively with 1 M HCl, saturated NaHCO3 and NaCl, After drying over anhydrous MgSO4 overnight, filtration, solvent removal, Separation on 200 - 300 mesh silica gel column chromatography (eluent DCM / MeOH = 10: 1) gave the white solid Oleic acid-Lys-OMe (compound 9).

Reference： [1]Patent: CN105056251,2018,B .Location in patent: Paragraph 0090; 0093; 0094
[2]Patent: CN104906076,2017,B .Location in patent: Paragraph 0093

29
[ 112-80-1 ]
[ 29110-74-5 ]
C₂₄H₃₇ClN₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	With copper(I) thiophene-2-carboxylate; (4,4'-di-tert-butyl-2,2'-dipyridyl)-bis-(5-methyl-2-(4-fluorophenyl)pyridine(-1H))-iridium(III) hexafluorophosphate; N,N,N?,N?-tetramethyl-N?-tert-butylguanidine; bathophenanthroline; iodomesitylene diacetate; In 1,4-dioxane; at 20℃; for 1h;Inert atmosphere; Irradiation;	General procedure: To a 20 ml or 40 ml viale quipped with a stir bar was added photocatalyst, nitrogen nucleophile, iodomesitylene dicarboxylate, copper salt, and ligand. Dioxane was added followed by addition of the base. The solution was sonicated for 1-3 min until it became homogeneous. Next, the solution was degassed by sparging with nitrogen for 5-10 min before sealing with Parafilm. The reaction was stirred and irradiated using two 34-W blue LED lamps (3 cm away, with cooling fan to keep the reaction at room temperature) for 1 h. The reaction mixture was removed from the light, cooled to ambient temperature, diluted with water (15 ml) and ethyl acetate (25 ml), and the aqueous layer was extracted with ethyl acetate (3 × 25 ml). The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified by flash chromatography on silica gel to afford the desired decarboxylative C-N coupling product. For aniline substrates, a solution of these nitrogen nucleophiles in dioxane was used; additionally, if the iodomesitylene dicarboxylate is a liquid, its solution in dioxane was used.

Reference： [1]Nature,2018,vol. 559,p. 83 - 88

30
[ 115-77-5 ]
[ 1070-34-4 ]
[ 112-80-1 ]
C₆₅H₁₁₆O₁₀ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
99%		In the reactor, 68.1g (0.5mol) of pentaerythritol, 423.8g (1.5mol) of oleic acid were added successively, and a catalyst was added, and a water agent was added to control the oil bath heating temperature of 130-135 C. Under nitrogen protection, the mixture was stirred and refluxed, and water was separated. After 3.0 to 4.0 hours, it was slightly cooled, and 80.4 g of monoethyl succinate (0.55 mol) was added thereto, and the temperature was raised to 130-135 C, and the reaction was stirred for 2 hours. After the reaction was completed, the mixture was cooled to room temperature, washed with water, and the organic layer was evaporated in vacuo to give a pale-yellow oily liquid. The acid value was 0.08 mg KOH/g, yield 99%.

Reference： [1]Patent: CN109053441,2018,A .Location in patent: Paragraph 0017

31
[ 112-80-1 ]
[ 91-20-3 ]
[ 187737-37-7 ]
[ 7373-13-9 ]
[ 74-85-1 ]
[ 112-61-8 ]
[ 95-47-6 ]
[ 611-14-3 ]
[ 106-42-3 ]
[ 100-41-4 ]
[ 62185-21-1 ]
[ 90-12-0 ]
[ 108-88-3 ]

Yield	Reaction Conditions	Operation in experiment
	With mesoporous ZSM-5 zeolite with pore size of about 16nm; at 550℃;Catalytic behavior;	General procedure: Catalytic performance of catalysts was evaluated by catalytic cracking of ethanol and oleic acid in a fixed-bed quartz tube reactor(inner diameter: 20 mm; length: 380 mm). As a typical run, the catalyst(0.5 g) was loaded into reactor, and heated to a desired temperature inN2 stream (the flow rate: 40 mL/min). The feedstock (0.87 g) was then injected into the reactor by a syringe pump. After flowing out from the reactor, the reaction products were cooled. Liquid products were weighed and analyzed by GC-MS (QP5000, Shimadzu, Japan) equipped with a DB-WAX fused silica capillary column (30m×0.25mm×0.25 mum). The gaseous product was collected with a gas collecting bag,and analyzed by GC referring to the method as described in our previous study

Reference： [1]Applied Catalysis A: General,2019,vol. 575,p. 101 - 110

32
[ 112-80-1 ]
[ 85342-65-0 ]
C₂₆H₃₃Cl₄NO₄ [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2019,vol. 141,p. 11398 - 11403

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P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 112-80-1 ]

Quality Control of [ 112-80-1 ]

Related Doc. of [ 112-80-1 ]

Product Details of [ 112-80-1 ]

Calculated chemistry of of [ 112-80-1 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 112-80-1 ]

Application In Synthesis of [ 112-80-1 ]

[ 112-80-1 ] Synthesis Path-Upstream 1~13

[ 112-80-1 ] Synthesis Path-Downstream 1~32

Similar Product of [ 112-80-1 ]

Related Functional Groups of [ 112-80-1 ]

Carboxylic Acids

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

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[ 112-80-1 ]

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[ 112-80-1 ]