[ CAS No. 112-86-7 ] {[proInfo.proName]}

Name: 112-86-7|(Z)-Docos-13-enoic acid|85%
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2D 3D

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Quality Control of [ 112-86-7 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 112-86-7 ]

Product Details of [ 112-86-7 ]

CAS No. :	112-86-7	MDL No. :	MFCD00063188
Formula :	C₂₂H₄₂O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	DPUOLQHDNGRHBS-KTKRTIGZSA-N
M.W :	338.57	Pubchem ID :	5281116
Synonyms :	Docosenoic acid (cis-13);cis-13-docosenoic acid;C22:1(cis-13)Fatty acid	Chemical Name :	(Z)-Docos-13-enoic acid

Calculated chemistry of [ 112-86-7 ]

Physicochemical Properties

Num. heavy atoms :	24
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.86
Num. rotatable bonds :	19
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	109.17
TPSA :	37.3 Å²

Pharmacokinetics

GI absorption :	Low
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-1.4 cm/s

Lipophilicity

Log Po/w (iLOGP) :	5.22
Log Po/w (XLOGP3) :	9.81
Log Po/w (WLOGP) :	7.67
Log Po/w (MLOGP) :	5.47
Log Po/w (SILICOS-IT) :	7.71
Consensus Log Po/w :	7.17

Druglikeness

Lipinski :	1.0
Ghose :	None
Veber :	1.0
Egan :	1.0
Muegge :	2.0
Bioavailability Score :	0.56

Water Solubility

Log S (ESOL) :	-6.87
Solubility :	0.0000462 mg/ml ; 0.000000136 mol/l
Class :	Poorly soluble
Log S (Ali) :	-10.51
Solubility :	0.0000000104 mg/ml ; 0.0 mol/l
Class :	Insoluble
Log S (SILICOS-IT) :	-6.99
Solubility :	0.000035 mg/ml ; 0.000000104 mol/l
Class :	Poorly soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	2.0
Synthetic accessibility :	3.53

Safety of [ 112-86-7 ]

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 [ 112-86-7 ]

* 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 [ 112-86-7 ]
Downstream synthetic route of [ 112-86-7 ]

[ 112-86-7 ] Synthesis Path-Upstream 1~3

1
[ 67-56-1 ]
[ 143-07-7 ]
[ 112-86-7 ]
[ 1120-34-9 ]
[ 111-82-0 ]

Reference： [1] Patent: EP2165998, 2010, A1, . Location in patent: Page/Page column 3-4

2
[ 67-56-1 ]
[ 112-86-7 ]
[ 1120-34-9 ]

Reference： [1] Journal of the Chemical Society, 1942, p. 481
[2] Recueil des Travaux Chimiques des Pays-Bas, 1936, vol. 55, p. 903,914
[3] Green Chemistry, 2017, vol. 19, # 15, p. 3535 - 3541
[4] Angewandte Chemie - International Edition, 2017, vol. 56, # 43, p. 13342 - 13346[5] Angew. Chem., 2017, vol. 129, p. 13527 - 13531,5

3
[ 112-86-7 ]
[ 18107-18-1 ]
[ 1120-34-9 ]

Reference： [1] Biochemistry, 2012, vol. 51, # 40, p. 7880 - 7890

[ 112-86-7 ] Synthesis Path-Downstream 1~51

1
[ 67-56-1 ]
[ 112-86-7 ]
[ 1120-34-9 ]

Reference： [1]Journal of the Chemical Society,1942,p. 481
[2]Green Chemistry,2017,vol. 19,p. 3535 - 3541
[3]Angewandte Chemie - International Edition,2017,vol. 56,p. 13342 - 13346
Angew. Chem.,2017,vol. 129,p. 13527 - 13531,5

2
[ 112-86-7 ]
[ 124-19-6 ]

Yield	Reaction Conditions	Operation in experiment
30.2%	With di-tert-butyl peroxide; C52H80CoN2O10; oxygen; In tetrahydrofuran; at 140℃; under 5250.53 Torr; for 5h;Autoclave;	3.4 g (0.01 mol) of erucic acid and 0.095 g (0.0001 mol) were added to the autoclave.a cobalt complex of an isosteric alcohol derivative, 34.0 g of tetrahydrofuran,1.6 g (0.012 mol) of t-butanol peroxide,Passing oxygen to the reactor pressure of 0.7 MPa, the reaction temperature is 140 C,The reaction time is 300 minutes.

Reference： [1]Patent: CN109553515,2019,A .Location in patent: Paragraph 0036; 0048; 0051
[2]Chemische Berichte,1923,vol. 56,p. 2056

3
[ 112-86-7 ]
[ 59044-32-5 ]

Yield	Reaction Conditions	Operation in experiment
	With oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane; at 0℃; for 3h;Inert atmosphere;	To a stirred solution of fatty acid in dichloromethane (DCM), catalytic amount of dimethyl formamide (DMF) was added and the contents were stirred at 0 C. Oxalyl chloride was added under nitrogen atmosphere and the reaction mixture was further stirred at 0 C for 3 h. Then reaction mixture was concentrated under reduced pressure to remove DCM and excess oxalyl chloride. Later crude acid chloride dissolved in DCM was used for the next step directly under nitrogen atmosphere.
	With oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane; at 0 - 20℃; for 3h;Inert atmosphere; Schlenk technique;	General procedure: To a stirred solution of the fatty acid (1 eq., 0.78 mmol) and a dropof DMF in dry dichloromethane (5 ml) was added dropwise oxalylchloride (3 eq., 297 mg, 2.34 mmol) at 0 C. The reaction mixture waswarmed slowly up to rt and stirred for further 3 h. Solvent and excessoxalyl chloride were removed in vacuo and the resulting acid chloridewas used next step without purification.

Reference： [1]Journal of the Indian Chemical Society,1969,vol. 46,p. 669 - 671
[2]Journal of Medicinal Chemistry,1993,vol. 36,p. 2595 - 2604
[3]Synthesis,2007,p. 3051 - 3055
[4]Analytical Chemistry,2012,vol. 84,p. 2388 - 2394
[5]Catalysis science and technology,2013,vol. 3,p. 429 - 435
[6]RSC Advances,2014,vol. 4,p. 2865 - 2872
[7]Bioorganic and Medicinal Chemistry Letters,2017,vol. 27,p. 3370 - 3373
[8]Bioorganic Chemistry,2019,vol. 84,p. 444 - 455

4
[ 112-86-7 ]
[ 616-01-3 ]

Reference： [1]MedChemComm,2015,vol. 6,p. 879 - 886
[2]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1991,vol. 30,p. 865 - 866
[3]Journal of the Chemical Society,1914,vol. 105,p. 2813
[4]Indian Journal of Chemistry,1966,vol. 4,p. 524 - 526
[5]Journal of labelled compounds and radiopharmaceuticals,2000,vol. 43,p. 243 - 250
[6]Synthesis,2011,p. 2357 - 2368
[7]Chemistry - A European Journal,2013,vol. 19,p. 15012 - 15018
[8]Journal of the American Chemical Society,2017,vol. 139,p. 8995 - 9000

5
[ 112-86-7 ]
[ 505-52-2 ]

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 5 Tridecanedioic acid 338.58 g (1 mol) of erucic acid (purity 95%) were ozonized in analogy to Example 1 and then hydrogenation was carried out. The hydrogenation solution obtained in this way contained nonanal and tridecanealdehyde acid and was divided by distillation. For oxidation, the corresponding aldehyde fraction was employed and was oxidized at 14 bar in analogy to Example 1. 185 g of tridecanedioic acid per cycle were obtained with a purity of 95%.

Reference： [1]ChemSusChem,2014,vol. 7,p. 2289 - 2294
[2]Tetrahedron Letters,2005,vol. 46,p. 3201 - 3203
[3]Chemische Berichte,1934,vol. 67,p. 295,297
[4]Journal of the American Chemical Society,1945,vol. 67,p. 1276
[5]Chemische Berichte,1923,vol. 56,p. 2056
[6]Journal of the Chemical Society,1927,p. 375
[7]Journal of the Chemical Society,1938,p. 1679
[8]Patent: US5686638,1997,A

6
[ 112-86-7 ]
[ 112-85-6 ]

Yield	Reaction Conditions	Operation in experiment
90.3%	With palladium 10% on activated carbon; hydrogen; In tetrahydrofuran; at 20 - 30℃; under 4500.45 - 6000.6 Torr;	13-Docosenoic acid (100 g) was suspended in THF (1500 ml) at 20-30C and hydrogenated in the presence of Palladium on charcoal (5 g, 10% w/w, 50 % wet) at 20-30 C over a hydrogen pressure of 6-8 Kg/cm . After completion of reaction the catalyst was filtered off, solvent was evaporated from the filtrate under reduced pressure (20-40 mm Hg) at 40-50 C to get a white colour residue. The above residue was suspended in methanol (1000 ml) and heated to 60-65C to obtain a clear solution and cooled to 20-30C slowly over a period of 30+5 min stirred for an hour at 20-30 C. The resulting solid was filtered and dried under reduced pressure (10-20 mm Hg) at 40-45 C to afford 90.83 g of Docosanoic acid. Yield: 90.3 % of theory Chromatographic purity (by GC): >98 %

Reference： [1]Patent: WO2018/220504,2018,A1 .Location in patent: Page/Page column 7; 8
[2]Patent: DE187788,
[3]Bulletin of the Chemical Society of Japan,1935,vol. 10,p. 138
Nippon Kagaku Kaishi,1935,vol. 56,p. 336
Chem.Abstr.,1935,p. 4330
[4]Journal of the American Chemical Society,1946,vol. 68,p. 231
[5]Journal of the American Chemical Society,1948,vol. 70,p. 366
[6]Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences,1909,vol. 149,p. 999
[7]Patent: DE187788,
[8]Bulletin de la Societe Chimique de France,1889,vol. <3>1,p. 296
[9]Journal of Biological Chemistry,1915,vol. 20,p. 527
[10]Monatshefte fur Chemie,1913,vol. 34,p. 1132
[11]Journal of the American Chemical Society,1926,vol. 48,p. 971
[12]Organic Process Research and Development,2012,vol. 16,p. 1307 - 1311

7
[ 112-86-7 ]
[ 5908-87-2 ]

Reference： [1]Journal of Biological Chemistry,1924,vol. 59,p. 921

8
[ 112-86-7 ]
[ 16317-09-2 ]

Yield	Reaction Conditions	Operation in experiment
42%	With 2Zn(2+)(CH3)3NC2H4OH(1+)5Cl(1-)=[HOC2H4N(CH3)3]Zn2Cl5; at 150℃; for 4h;	(a) gamma-undecalactone: A mixture of 10-undecenylic acid (2.0 g; 10.8 mmol) and IL (2.23 g; 5.4 mmol) was stirred at 130 C. After 8 h, the product was separated from IL by extracting first with ethyl acetate then with hexane. The organic solvent was evaporated using rotary evaporator and dried under vacuum to get 1.88 g of peach flavored gamma-undecalactone as clear oil (isolated yield, 94%). The structure of the product was confirmed by 1H and 13C NMR, ESI-Mass and matched well with literature report.81H NMR (300 MHz, CDCl3, delta): 4.46 (tt, 1H, CH-O), 2.51 (dd, 2H, alpha-CH2), 2.31-2.26 (m, 1H, beta-CH2), 1.90-1.75 (m, 1H, beta-CH2), 1.75-1.60 (m, 1H, delta-CH2), 1.60-1.50 (m,1H, delta-CH2), 1.40-1.20 (m, 10H, 5CH2), 0.85 (t, 3H, CH3). 13C NMR (75 MHz, CDCl3, delta):14.0-29.5 (CH2), 31.8 (beta-CH2), 35.5 (alpha-CH2), 81.1 (CH-O), 177.1 (C=O). ESI-Mass m/z: [m++Na] 207, [m++1+Na] 208. (b) gamma-stearolactone: A mixture of oleic acid (2 g, 7.8 mmol) and IL (2.9 g, 7.8 mmol) was stirred at 150 C. After 4 h, the product was separated from IL by extracting first with a binary mixture of ethyl acetate and hexane (30:70) and finally with hexane. The organic solvent was evaporated to get 1.73 g of crude product, which was crystallized from acetone at -20 C to get 1.48 g of gamma-stearolactone as white solid (isolated yield, 74%). The structure of the product was confirmed by 1H and 13C NMR, ESI-Mass and matched well with literature report.41H NMR (300 MHz, CDCl3, delta): 4.46 (tt, 1H, CH-O), 2.51 (dd, 2H, alpha-CH2), 2.31-2.26(m, 1H, beta-CH2), 1.90-1.75 (m, 1H, beta-CH2), 1.75-1.60 (m, 1H, delta-CH2), 1.60-1.50 (m, 1H, delta-CH2), 1.40-1.10 (m, 24H, 12CH2), 0.85 (t, 3H, CH3). 13C NMR (75 MHz, CDCl3, delta):14.0-29.5 (CH2), 31.8 (beta-CH2), 35.5 (alpha-CH2), 81.1 (CH-O), 177.1 (CO). ESI-Mass m/z: [m++Na] 305.3, [m++1+Na] 306.3. (c) gamma-erucalactone: A mixture of erucic acid (2 g, 5.9 mmol) and IL (2.42 g, 5.9 mmol) was stirred at 150 C. After 4 h, the product was separated from IL by extracting first with ethyl acetate and then with hexane. The organic solvent was evaporated to get 1.86 g of crude product, which was crystallized from acetone at -20 C to get 0.8 g of gamma-erucalactone as white solid (isolated yield is 42%). The structure of the product was confirmed by 1H NMR, 13C NMR and ESI-Mass. 1H NMR (300 MHz, CDCl3, delta): 4.46 (tt, 1H, CH-O), 2.51 (dd, 2H, alpha-CH2), 2.31-2.26(m, 1H, beta-CH2), 1.90-1.75 (m, 1H, beta-CH2), 1.75-1.60 (m, 1H, delta-CH2), 1.60-1.50 (m,1H, delta-CH2), 1.40-1.10(m, 32H, 16CH2), 0.85 (t, 3H, CH3). 13C NMR (75 MHz, CDCl3, delta):14.0-29.5 (CH2), 31.8 (beta-CH2), 35.5 (alpha-CH2), 81.1 (CH-O), 177.1 (CO). ESI-Mass m/z: [m++Na] 361.4, [m++1+Na] 362.4.

Reference： [1]Tetrahedron Letters,2012,vol. 53,p. 3471 - 3473
[2]Zhurnal Russkago Fiziko-Khimicheskago Obshchestva,1908,vol. 40,p. 836
Chemisches Zentralblatt,1908,vol. 79,p. 1414

9
[ 112-86-7 ]
[ 7541-49-3 ]
[ 72996-22-6 ]

Reference： [1]Patent: DE2812978,1979,
Chem.Abstr.,1980,vol. 92

10
[ 112-86-7 ]
[ 629-98-1 ]

Reference： [1]Tetrahedron Asymmetry,2005,vol. 16,p. 3176 - 3182
[2]Letters in Organic Chemistry,2012,vol. 9,p. 628 - 631
[3]Journal of the Chemical Society,1960,p. 4514 - 4521
[4]Journal of general chemistry of the USSR,1964,vol. 34,p. 1662 - 1665
Zhurnal Obshchei Khimii,1964,vol. 34,p. 1651 - 1655

11
[ 112-86-7 ]
[ 7735-38-8 ]

Reference： [1]Organic and Biomolecular Chemistry,2018,vol. 16,p. 5771 - 5779
[2]Synthetic Communications,1994,vol. 24,p. 1265 - 1269
[3]Angewandte Chemie - International Edition,2000,vol. 39,p. 1934 - 1937
[4]Chemistry - A European Journal,2003,vol. 9,p. 282 - 290
[5]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 3426 - 3430

12
[ 112-86-7 ]
[ 100-79-8 ]
[ 69466-23-5 ]

Yield	Reaction Conditions	Operation in experiment
	With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 0 - 20℃; for 16h;	General procedure: For reaction 1-To a solution of the desired free fatty acid (1.0equivalent) and 1,2-isopropylideneglycerol (1.0 equivalent) inanhydrous dichloromethane (CH 2 Cl 2 , 1.5 ml) maintained at0 C, N,N-dimethyl-4-aminopyridine (0.25 equivalent) andEDC HCl (1.0 equivalent) was sequentially added. The reactionmixture was warmed to room temperature and stirred for 16 h.Upon disappearance of starting compound observed on TLC,the reaction was quenched with saturated sodium bicarbonate(NaHCO 3 ) and extracted three times with CH 2 Cl 2 . The combinedorganic layer was dried over sodium sulfate (Na 2 SO 4 ) and filtered,and the filtrate was concentrated. The crude residue was purifiedby column chromatography using 5% ethyl acetate/hexane as aneluent to afford the corresponding fatty acid ester. For reaction 2-Amberlyst-15 (Hform, 0.5 equivalent) wasadded to a solution of fatty acid ester (1.0 equivalent) in MeOH.The resulting reaction mixture was stirred for 16 h at roomtemperature. After completion of reaction (TLC analysis),Amberlyst-15 was filtered off, and the filtrate was evaporatedunder reduced pressure. The crude residue was purified by col-umn chromatography using 40% ethyl acetate/hexane as an elu-ent to afford the corresponding 1-MAG lipid. The detailed syn-thesis and compound characterization data of each individual1-MAG lipid can be found in the supporting information.

Reference： [1]Journal of the American Oil Chemists' Society,1995,vol. 72,p. 1301 - 1307
[2]Journal of Biological Chemistry,2018,vol. 293,p. 16953 - 16963

13
[ 112-86-7 ]
(Z)-Docos-13-enal [ No CAS ]

Reference： [1]Chemistry Letters,1998,p. 1143 - 1144
[2]Bulletin of the Chemical Society of Japan,2001,vol. 74,p. 1803 - 1815
[3]Angewandte Chemie - International Edition,2017,vol. 56,p. 13342 - 13346
Angew. Chem.,2017,vol. 129,p. 13527 - 13531,5

14
[ 112-86-7 ]
[ 53481-03-1 ]
[ 5557-31-3 ]

Yield	Reaction Conditions	Operation in experiment
70%		Synthesis of 1,26-hexacos-13-enedioic acid (5d): Diacid 5d was synthesized from 3d as above. The pure diacid was obtained by recrystallization from acetone in a yield of 70%, m.p.=105-107.5 C. (lit. m.p.=96 C. (Van Dam, P. B., et al., J. Am. Oil. Chem. Soc., 51: 389-391 (1974)). 1H NMR (CD3OD, 200 MHz): delta 5.4 (m, CHCH, 2H), 2.28 (t, J=7.4 Hz & 7.4 Hz, CH2CO2H, 4H), 1.97 (m, CH2CHCH, 4H), 1.6 (m, 4H), 1.30 (m, 32H). 13C NMR (CD3OD, 50 MHz): delta 177.9 (s, -CO2H), 131.7 (s, -CHCH-), 35.2 (s), 33.7 (s), 30.9 (s), 30.8 (s), 30.78 (s), 30.7 (s), 30.6 (s), 30.4 (s), 30.3 (s), 26.3 (s). The methyl ester of diacid 5d was analyzed by GC/MS (retention time t=28.2 min) and had an [M]+ of m/z 452 (calc., [M]+ m/z 452.38).

Reference： [1]Journal of the American Oil Chemists' Society,2006,vol. 83,p. 629 - 634
[2]Patent: US7534917,2009,B1 .Location in patent: Page/Page column Sheet 2/6; 7; 17

15
[ 629-98-1 ]
[ 112-86-7 ]
erucyl erucate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
93%	With choline chloride; zinc(II) chloride at 110℃; for 12h;

Reference： [1]Sunitha, Sadula; Kanjilal, Sanjit; Reddy, P. Srinivasa; Prasad, Rachapudi B.N. [Tetrahedron Letters, 2007, vol. 48, # 39, p. 6962 - 6965]

16
[ 112-86-7 ]
[ 4568-88-1 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 3426 - 3430
[2]Chemistry - A European Journal,2003,vol. 9,p. 282 - 290
[3]Angewandte Chemie - International Edition,2000,vol. 39,p. 1934 - 1937

17
[ 112-86-7 ]
[ 15462-16-5 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2007,vol. 17,p. 3426 - 3430

18
[ 112-86-7 ]
[ 488117-69-7 ]

19
[ 112-86-7 ]
[ 512180-40-4 ]

20
[ 112-86-7 ]
[ 60037-58-3 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1: 91 percent / 30percent H₂O₂, HCOOH 2: 89 percent / aq. Na₂CO₃, H₃PO₄, NaIO₄ 3: 1.) NaH, DMSO 4: PTS 5: 90 percent / LiAlH₄ (LAH) / diethyl ether 6: 100 percent / pyridine / 24 h / Ambient temperature

Reference： [1]Subbaraman, A S; Mithran, S; Mamdapur, V R [Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 1991, vol. 30, # 9, p. 865 - 866]

21
[ 112-86-7 ]
[ 1460-18-0 ]

Reference： [1]Indian Journal of Chemistry,1966,vol. 4,p. 524 - 526

22
denatonium hydroxide [ No CAS ]
[ 112-86-7 ]
[ 890843-19-3 ]

Yield	Reaction Conditions	Operation in experiment
100%	In methanol; at 30 - 60℃; for 1 - 2h;	EXAMPLE 7; - Preparation of fatty derivative salts from pure quaternary hydroxide (denatonium eruciate); 50 grams (0.1462 mol) of denatonium hydroxide was dissolved in 50 ml of methanol at 30-45 C. A solution of 54.5 gram (0.1462 mol i.e. 1 mole erucic acid against 1 mol denatonium hydroxide) of erucic acid (with 90.7 % assay) in 50 ml of methanol was added at 30-45 C, and the thus obtained mixture was stirred for 1 - 2 hours at 45-60 C temperature. The solvent was then distilled off up to yellow thick semi solid mass. 101 grams of denatonium eruciate was obtained with a quantitative yield. (Assay = 99.09%, S' Ash = 0.08%).

Reference： [1]Patent: WO2006/62406,2006,A2 .Location in patent: Page/Page column 9

23
[ 112-86-7 ]
[ 857197-45-6 ]

Yield	Reaction Conditions	Operation in experiment
82%	With sulfuric acid; In toluene;	EXAMPLE VI Five-hundred grams molten erucic acid were slowly added to a mixture of 679 gms toluene and 723 gms concentrated sulfuric acid while maintaining the temperature below 10 C. Tolyldocosanoic acid (acid value 123) was obtained in 82% yield.

Reference： [1]Patent: US4356315,1982,A

24
[ 112-86-7 ]
[ 109-55-7 ]
[ 149968-48-9 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium hydroxide; at 160℃; for 12h;Inert atmosphere;	erucic acid, purity 90% (W),Bellingham Technology Co., Ltd.; N, N-dimethylaminopropylamine,N, N-ethylaminopropylamine, purity 90% (W),Shanghai Jing Chun Biochemical Technology Co. 3-bromo-1-propanol, purity 95% (W)Shaoyuan (Shanghai) Chemical Technology Co.Potassium hydroxide, analytical grade, Sinopharm Group Chemical Reagent Co.Nicolet 6700 Fourier transform infrared spectrometer,Thermo Fisher Scientific;RS6000 Huck Rotational Rheometer,Quadruple LC / MS 6120 LC / MS,Agilent Technologies.Comprising the steps of: (1) Erucic acid was added to a three-neck flask equipped with a reflux condenser and a stirrerN, N-dimethylaminopropylamine (or N, N-ethylaminopropylamine), (2) under argon(3) After completion of the reaction, unreacted N, N-dimethylaminopropylamine (or N, N-ethylaminopropylamine) was removed by rotary evaporation.The product erucic amide propyl dimethyl (ethyl) amine.

Reference： [1]RSC Advances,2015,vol. 5,p. 19135 - 19144
[2]Synlett,2009,p. 2655 - 2658
[3]Journal of Surfactants and Detergents,2012,vol. 15,p. 657 - 661
[4]Journal of Surfactants and Detergents,2014,vol. 17,p. 295 - 301
[5]RSC Advances,2016,vol. 6,p. 88426 - 88432
[6]Patent: CN105566144,2016,A .Location in patent: Paragraph 0004

25
[ 67-56-1 ]
[ 143-07-7 ]
[ 112-86-7 ]
[ 1120-34-9 ]
[ 111-82-0 ]

Yield	Reaction Conditions	Operation in experiment
	gel-type acidic ion exchange resin; In canola oil; at 60 - 67℃; under 760.051 Torr;Molecular sieve;	Example 1: Selective Esterification; Comparing fatty acids with differing chain lengths; In a four-neck 1L RB flask equipped with a Soxhlet condenser containing 50 g activated molecular sieves 3A, thermometer and mechanical stirrer, was added dry polymeric catalyst (13.75 g, 5% by weight of reaction mixture). Canola oil (202.5 g, 0.23 moles triglycerides) was charged to the flask and mechanical stirring started at 185 RPM. Then, erucic acid (37.9g, 0.112 moles) and lauric acid (22.4 g, 0.112 moles) were added and the flask was heated by external infrared lamp to reach 60 C over 20 minutes. At 60 C, methanol (4 g, 0.13 mole or 1.1 equivalent of lauric acid) was charged to the flask. The mixture was allowed to reach reflux temperature (?65-67C) with efficient stirring (235 rpm). The reflux was condensed through a water condenser and passed through the molecular sieves back into the flask. The reaction was carried out at 65C-67C (reflux temperature) and atmospheric pressure for 30 min. After 30 min., the mixture was cooled to ambient temperature. The catalyst was recovered by filtration from the organic phase. Conversion of specific acids is summarized in Table 1

Reference： [1]Patent: EP2165998,2010,A1 .Location in patent: Page/Page column 3-4

26
[ 51-61-6 ]
[ 112-86-7 ]
[ 565186-21-2 ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: All fatty acid amides with different acyl chains and amine heads were synthesized using the same procedure but with different precursor compounds. 2-(1H-Benzotriazole-1-yl)-1,2,3,3-tetramethyluronium tetrafluoroborate (TBTU, 1 equiv) was added to a mixture of compound C1 (1 equiv) and triethylamine (TEA, 2 equiv) in EtOAc. After stirring for 1 h at room temperature, isopropylamine (2 equiv) was added and the reaction mixture was stirred for 12 h. The mixture was washed with water, dried and concentrated to give a residue that was purified by reversed-phase HPLC (YMC ODS-H80) eluting with 80% aqueous CH3CN to yield compound 1 (1.5 mg, 63%);