[ CAS No. 13108-19-5 ] {[proInfo.proName]}

Name: 13108-19-5|10-Aminodecanoic acid|97%
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Quality Control of [ 13108-19-5 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 13108-19-5 ]

SDS Specification

Alternatived Products of [ 13108-19-5 ]

Product Details of [ 13108-19-5 ]

CAS No. :	13108-19-5	MDL No. :	MFCD00270349
Formula :	C₁₀H₂₁NO₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	XAUQWYHSQICPAZ-UHFFFAOYSA-N
M.W :	187.28	Pubchem ID :	83150
Synonyms :

Calculated chemistry of [ 13108-19-5 ]

Physicochemical Properties

Num. heavy atoms :	13
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.9
Num. rotatable bonds :	9
Num. H-bond acceptors :	3.0
Num. H-bond donors :	2.0
Molar Refractivity :	54.66
TPSA :	63.32 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-8.56 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.09
Log Po/w (XLOGP3) :	-1.57
Log Po/w (WLOGP) :	2.15
Log Po/w (MLOGP) :	1.7
Log Po/w (SILICOS-IT) :	1.85
Consensus Log Po/w :	1.24

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	0.58
Solubility :	715.0 mg/ml ; 3.82 mol/l
Class :	Highly soluble
Log S (Ali) :	0.75
Solubility :	1050.0 mg/ml ; 5.6 mol/l
Class :	Highly soluble
Log S (SILICOS-IT) :	-2.54
Solubility :	0.541 mg/ml ; 0.00289 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	2.0
Synthetic accessibility :	1.6

Safety of [ 13108-19-5 ]

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

Application In Synthesis of [ 13108-19-5 ]

* 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.

Downstream synthetic route of [ 13108-19-5 ]

[ 13108-19-5 ] Synthesis Path-Downstream 1~74

1
[ 67-56-1 ]
[ 13108-19-5 ]
[ 106590-42-5 ]

Yield	Reaction Conditions	Operation in experiment
89%	With acetyl chloride; at 0℃; for 3h;Inert atmosphere; Reflux;	Freshly distilled acetyl chloride (1.70 mL, 23.90 mmol) was added dropwise to a stirred suspension of <strong>[13108-19-5]10-aminodecanoic acid</strong> 12 (1.80 g, 9.61 mmol) in anhydrous MeOH (20 mL) under N2 atmosphere at 0 °C. Once the addition was complete, the mixture was heated under reflux for 3 h. After completion of the reaction, the solvent and excess acetyl chloride were distilled off under reduced pressure affording the corresponding methyl 10-aminodecanoate as a white solid (89percent), which was used in the next reaction without further purification. Lithium aluminum hydride (1.65 g, 17.20 mmol) was added in small portions to a stirred suspension of the amino ester intermediate (1.73 g, 8.57 mmol) in anhydrous THF (100 mL) at 0 °C. The reaction mixture was heated under reflux for 48 h, then cooled to room temperature and poured into crushed ice. The aqueous layer was vigorously extracted with CH2Cl2 (6 x 80 mL) and the combined organic phases were washed with brine and dried over anhydrous Na2SO4. The solvent was evaporated under reduced pressure and the crude product was recrystallized to obtain pure 16 (0.92 g, 62percent).

Reference： [1]European Journal of Medicinal Chemistry,2015,vol. 101,p. 367 - 383
[2]Anales de la Real Sociedad Espanola de Fisica y Quimica, Serie B: Quimica,1950,vol. 46,p. 727,731

2
[ 123-99-9 ]
[ 13108-19-5 ]

Reference： [1]Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences,1906,vol. 143,p. 362

3
[ 1009-89-8 ]
[ 13108-19-5 ]

Reference： [1]Anales de la Real Sociedad Espanola de Fisica y Quimica, Serie B: Quimica,1950,vol. 46,p. 727,731

4
[ 35147-40-1 ]
[ 13108-19-5 ]

Reference： [1]Journal of Polymer Science,1948,vol. 3,p. 85,89
[2]Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya,1946,p. 68
Chem.Abstr.,1948,p. 5849

5
[ 99175-22-1 ]
[ 13108-19-5 ]

Reference： [1]Zhurnal Obshchei Khimii,1957,vol. 27,p. 2418,2422;engl.Ausg.S.2481,2484

6
[ 37027-56-8 ]
[ 13108-19-5 ]

Reference： [1],1958,vol. 5,p. 53,59
Chem.Abstr.,1961,p. 10310

7
[ 5810-19-5 ]
[ 13108-19-5 ]

Reference： [1]Kogyo Kagaku zasshi / Journal of the Society of Chemical Industry,1954,vol. 57,p. 769
Chem.Abstr.,1955,p. 10234
[2]Patent: US2839547,1956,

8
[ 91017-32-2 ]
[ 13108-19-5 ]

Reference： [1]Patent: US2862940,1953,
[2]Canadian Journal of Chemistry,1962,vol. 40,p. 1189 - 1195

9
[ 105474-03-1 ]
[ 13108-19-5 ]

Reference： [1]Zhurnal Obshchei Khimii,1958,vol. 28,p. 2520,2522; engl. Ausg. 2556, 2558
[2]Tetrahedron,1962,vol. 18,p. 21 - 36

10
[ 103799-79-7 ]
[ 13108-19-5 ]

Reference： [1]Biochemical Journal,1937,vol. 31,p. 1376,1377

11
[ 112-38-9 ]
[ 13108-19-5 ]

Reference： [1]Canadian Journal of Chemistry,1962,vol. 40,p. 1189 - 1195
[2]Canadian Journal of Chemistry,1962,vol. 40,p. 1189 - 1195

12
[ 108-31-6 ]
[ 13108-19-5 ]
10-((Z)-3-Carboxy-acryloylamino)-decanoic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 1692 - 1703

Yield	Reaction Conditions	Operation in experiment
		EXAMPLE 9 STR86 5R, 20S, 23S-3-(5-BENZYL-4, 7, 18, 19, 22-PENTAOXOCYCLOEICOSAHYDRO-3A, 6, 17,[21-TETRAAZACYLOPENTACYCLOHENEICOSEN-20-YL)PROPYL]GUANIDINE TRIFLUOROACETIC ACID HYDRATE COMPOUND 9 A slurry of 9-cyanopelargonic acid (8.6 g, 48 mrnol), a catalytic amount 5percentRh/Al2 O3, and 200 mL of 2.0N NH3 -EtOH was shaken under 50 psig of H2 pressure for 6 h, then filtered through dicalite. The filter pad was washed with 100 mL of hot 1:1 MeOH--H2 O, and the combined filtrates were concentrated to give 6.1 g of 10-aminodecanoic acid.

14
9-cyano-nona-3<i>t</i>,7<i>t</i>-dienoic acid methyl ester [ No CAS ]
[ 13108-19-5 ]

Reference： [1]Gazzetta Chimica Italiana,1959,vol. 89,p. 1390,1395

15
oxime of/the/ κ-oxo-palmitic acid [ No CAS ]
[ 13108-19-5 ]

Reference： [1]Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan,1925,p. 6
Chemisches Zentralblatt,1926,vol. 97,p. 916

16
convolvulinoloic acid [ No CAS ]
[ 123-99-9 ]
[ 13108-19-5 ]

Reference： [1]Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan,1925,p. 4
Chemisches Zentralblatt,1926,vol. 97,p. 915

17
[ 103799-79-7 ]
[ 7664-93-9 ]
[ 14130-05-3 ]
[ 13108-19-5 ]
[ 1852-04-6 ]
[ 506-30-9 ]

Reference： [1]Biochemical Journal,1937,vol. 31,p. 1376,1377

18
[ 75-77-4 ]
[ 13108-19-5 ]
[ 1026483-48-6 ]

Reference： [1]Journal of Medicinal Chemistry,2000,vol. 43,p. 3573 - 3576

19
polymer; monomer(s): 4-methoxysalicylic acid [ No CAS ]
[ 13108-19-5 ]
N-(4-methoxysalicyloyl)-10-aminodecanoic acid [ No CAS ]

Reference： [1]Synthetic Communications,2005,vol. 35,p. 1567 - 1575

20
poly(3,5-dichlorosalicylate) [ No CAS ]
[ 13108-19-5 ]
N-(3,5-dichlorosalicyloyl)-10-aminodecanoic acid [ No CAS ]

Reference： [1]Synthetic Communications,2005,vol. 35,p. 1567 - 1575

21
[ 13108-19-5 ]
10-benzoylamino-decanoic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2000,vol. 43,p. 3573 - 3576

22
[ 13108-19-5 ]
C₂₀H₃₃NO₃Si [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2000,vol. 43,p. 3573 - 3576

23
[ 13108-19-5 ]
10-(2,5-Dioxo-2,5-dihydro-pyrrol-1-yl)-decanoic acid [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1996,vol. 39,p. 1692 - 1703

24
[ 1871-96-1 ]
[ 13108-19-5 ]

Reference： [1]Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya,1946,p. 68
Chem.Abstr.,1948,p. 5849

25
[ 3930-10-7 ]
[ 13108-19-5 ]

Reference： [1]Zhurnal Obshchei Khimii,1957,vol. 27,p. 2418,2422;engl.Ausg.S.2481,2484

26
[ 1561-48-4 ]
[ 13108-19-5 ]

Reference： [1]Zhurnal Obshchei Khimii,1957,vol. 27,p. 2418,2422;engl.Ausg.S.2481,2484

27
[ 100131-38-2 ]
[ 13108-19-5 ]

Reference： [1]Zhurnal Obshchei Khimii,1957,vol. 27,p. 2418,2422;engl.Ausg.S.2481,2484

28
[ 21010-06-0 ]
[ 13108-19-5 ]

Reference： [1]Zhurnal Obshchei Khimii,1958,vol. 28,p. 2520,2522; engl. Ausg. 2556, 2558

29
[ 71877-34-4 ]
[ 13108-19-5 ]

Reference： [1]Zhurnal Obshchei Khimii,1958,vol. 28,p. 2520,2522; engl. Ausg. 2556, 2558

30
[ 100132-35-2 ]
[ 13108-19-5 ]

Reference： [1]Zhurnal Obshchei Khimii,1958,vol. 28,p. 2520,2522; engl. Ausg. 2556, 2558

31
[ 78845-71-3 ]
[ 13108-19-5 ]

Reference： [1]Zhurnal Obshchei Khimii,1958,vol. 28,p. 2520,2522; engl. Ausg. 2556, 2558

32
[ 100370-91-0 ]
[ 13108-19-5 ]

Reference： [1]Zhurnal Obshchei Khimii,1958,vol. 28,p. 2520,2522; engl. Ausg. 2556, 2558
[2]Tetrahedron,1962,vol. 18,p. 21 - 36

33
[ 103565-56-6 ]
[ 13108-19-5 ]

Reference： [1]Zhurnal Obshchei Khimii,1958,vol. 28,p. 2520,2522; engl. Ausg. 2556, 2558

34
[ 41059-02-3 ]
[ 13108-19-5 ]

Reference： [1]Kogyo Kagaku zasshi / Journal of the Society of Chemical Industry,1954,vol. 57,p. 769
Chem.Abstr.,1955,p. 10234

35
[ 13108-19-5 ]
[ 501-53-1 ]
[ 195302-79-5 ]

Yield	Reaction Conditions	Operation in experiment
	In sodium hydroxide; water; acetonitrile;	The crude product (5.7 g) was dissolved in 15.5 mL of 2N NaOH and treated simultaneously with 23 mL of 2N NaOH and 5.8 g of carbobenzoxychloride at 0° C. with vigorous stirring over 0.5 h. Water and 2N NaOH were added as needed to maintain stirring and a pH between 10-14. After stirring for 2.5 h, the reaction was diluted with 400 mL of H2 O and filtered through dicalite. The filtrate was acidified (pH 2) with H2 SO4, then extracted with ether. The combined ether extracts were dried (Na2 SO4), filtered and concentrated. The residue was dissolved in CH3CN, filtered, and the filtrate concentrated to afford 5.3 g of 10-(N-carbobenzoxy)-aminodecanoic acid which was used without further purification: FAB-MS m/z 322 (MH+). Compound 9 was prepared using the general method of Example 1. CBZ-D-PheOH replaced CBZ-D-homophenylalanine in Step 1a and 10-(N-carbobenzoxy)-aminodecanoic acid replaced 8-carbobenzoxyaminooctanoic acid in Step 1c to give the title compound as a solid: FAB-MS m/z 598 (MH+); Anal Calc'd for C31 H47 N7 O5.1.75 C2 HF3 O2.1.75 H2 O; Calc'd: C, 50.00; H, 6.35; N, 11.83; H2 O, 3.80; Found: C, 49.62; H, 6.23; N, 11.93; H2 O, 3.46.

Reference： [1]Patent: US5888971,1999,A

36
[ 23810-52-8 ]
[ 13108-19-5 ]
[ 186822-49-1 ]

Reference： [1]Russian Chemical Bulletin,1996,vol. 45,p. 2661 - 2662

37
[ 13108-19-5 ]
[ 920-46-7 ]
[ 59178-93-7 ]

Yield	Reaction Conditions	Operation in experiment
92%	With sodium carbonate; In tetrahydrofuran; water; at 0℃; for 5h;	Example 1; [0049] Synthesis of 11 -Methacrylamidoundecanoic Acid; 10-Aminodecanoic acid (4.04 g, 20 mmol) was dissolved in 300 ml of THF and water (1 :1 ) in an ice-water bath, and then sodium carbonate (3.18 g, 30 mmol) was added. Methacryloyl chloride (3.15 g, 30 mmol) was slowly added, and the mixture was <n="28"/>stirred for 5 h. After reaction was complete, the solution was neutralized to pH 5 with HCI. Then the solvent was removed by evaporation, and the residue was extracted with 200 ml CH2CI2, producing a white solid. Recrystallization from a hexane/ethyl acetate solution gave 4.96 g product (yield 92percent). Alternatively, replacing THF/H2O with CHCI3 gave a similar or higher yield.Analysis: 1HNMR (CDCI3, 400 MHz) delta: 5.69 (s, 1 H, CHH=), 5.32 (s, 1 H, CHH=), 3.30 (m, 2H, NHCH2CH2), 2.34 (t, 2H, J = 7.4 Hz, CH2CH2COOH), 1.97 (s, 3H, CH2=CHCH3), 1.48-1.70 (m, 4H, NHCH2CH2CH2 and CH2CH2CH2COOH), 1.24-1.38 (m, 12H, NHCH2CH2(CH2)6CH2CH2COOH). 13C-NMR (CDCI3, 400 MHz) delta: 179.50 (COOH), 168.86 (CH2=CCH3CONHCH2), 140.26 (CH2=CCH3CONHCH2), 119.67 (CH2=CCH3), 40.00 (CH2=CCH3CONHCH2CH2), 34.29 (CH2CH2COOH), 29.70, 29.57, 29.47, 29.40, 29.35, 29.19, 27.10, 24.90(CH2=CCH3CONHCH2(CH2)8CH2COOH), 18.92 (CH2=CCH3). ESMS (THF/H2O, negative ion): m/z = 268.2 ([M-H]", calculated: 268.2).

Reference： [1]Patent: WO2008/100907,2008,A2 .Location in patent: Page/Page column 26-27

38
[ 13108-19-5 ]
[ 320-72-9 ]
N-(3,5-dichlorosalicyloyl)-10-aminodecanoic acid [ No CAS ]
C₁₉H₂₇Cl₂NO₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Preparation of Compound 4; [0054] Acetic anhydride (7.10 mL, 7.69 g, 75.0 mmol. 1.04 eq), <strong>[320-72-9]3,5-dichlorosalicylic acid</strong> (15.0 g, 72.5 mmol, 1.00 eq), and xylenes (40 mL) were added to a 250 mL, three-neck flask fitted with a magnetic stir bar, a thermometer, and a Dean-Stark trap with condenser. The flask was placed in a heating mantle, and heating of the cloudy white mixture begun. The reaction mixture became a clear solution around 100° C. Most of the volatile organics (xylenes and acetic acid) were distilled into the Dean-Start trap over three hours (135-146° C.). Distillation was continued for another hour (a total of 50 mL distilled), during which the pot temperature slowly rose to 165 C. and the distillate slowed to a trickle. The residue was poured off while still hot into an aluminum tray. Upon cooling a brittle yellow glass formed. The solid was ground to a fine powder. The oligo (3,5-dichlorosalicylate) produced was used without further purification. [0055] A slurry of 3.0 g of (16.0 mmol, 1.1 eq) 10-aminodecanoic acid, 9 ml (18.0 mmol, 1.13 eq) of 2 N aqueous sodium hydroxide and 30 ml of dioxane was added to a white slurry of 3.97 g (20.8 mmol, 1.3 eq) of oligo (3,5-dichlorosalicylate) and 30 ml of dioxane in a 250 mL round bottom flask equipped with a magnetic stir bar and reflux condenser. The reaction mixture was heated to 90° C. for 20 hours (at which time no further change was observed, by HPLC). The reaction mixture was cooled to 250° C. and acidified to pH=1 with 2N aqueous hydrochloric acid. The mixture was concentrated in vacuo (60 C., 50 mm). The resulting solid was recrystallized twice from ethanol-water decolorized with charcoal but was not yet clean. Column chromatography using 5:1 hexanes/ethyl acetate-1percent acetic acid as eluant gave one fraction as acid and another as ethyl ester. The ethyl ester was hydrolyzed to the acid using 4 ml of 2N aqueous sodium hydroxide and acidified with 2N aqueous hydrochloric acid. The acid was isolated by filtration. The combined acid portions were triturated with methylene chloride and hexanes to give 1.22 g of N-(3,5-dichlorosalicyloyl)-10-aminodecanoic acid.

Reference： [1]Patent: US2003/216589,2003,A1 .Location in patent: Page/Page column 6

39
[ 13108-19-5 ]
[ 24424-99-5 ]
[ 173606-50-3 ]

Yield	Reaction Conditions	Operation in experiment
2.42 g	With sodium hydroxide; In water; tert-butyl alcohol; at 20℃; for 24h;	The crude product from the previous step was placed in a 100-mL round-bottom flask with a magnetic stirbar, and NaOH (505 mg, 12.6 mmol) and Boc anhydride (2.31 g, 10.6 mmol) were added. Water (11 mL) and t-butanol (5 mL) were added to the flask to dissolve the solids, and the mixture was stirred at rt for 24 h. The crude product was diluted with water (20 mL) and 1 M HCl (20 mL). The resulting mixture was extracted with ethyl acetate (30 mL, 2x) and brine (30 mL). The organic layer was isolated, dried over MgSO4, and concentrated in vacuo to yield 2.42 g of 2 as a white solid (84percent isolated yield). The 1H NMR and 13C NMR spectra for acid 2 were identical to those that were previously reported.

Reference： [1]Journal of the American Chemical Society,2009,vol. 131,p. 10610 - 10619
[2]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 5054 - 5057
[3]Organic and Biomolecular Chemistry,2014,vol. 12,p. 8132 - 8137

40
[ 50530-12-6 ]
[ 13108-19-5 ]

Yield	Reaction Conditions	Operation in experiment
100%	With ammonia; In water; at 20℃; for 24h;	10-bromodecanoic acid (2.51 gr, 10 mmol) was added to a round bottom flask containing 80 mL of aqueous ammonium hydroxide (25percent NH3). The resulting mixture was stirred for 24 hours at room temperature, after which the aqueous solution was evaporated under reduced pressure, resulting in 8b as a white solid at quantitative yield. 1H-NMR (200 MHz, CD3OD): 1.25-1.4 (m; 10H), 1.5-1.7 (m; 4H), 2.15 (t; /= 7.38 Hz; 2H), 2.89 (t; /= 7.48 Hz; 2H).
	With ammonium hydroxide; water; at 20℃; for 24h;	In a 250-mL round-bottom flask equipped with a magnetic stirbar, 10-bromodecanoic acid (2.51 g, 10.0 mmol) was dissolved in 80 mL of aqueous ammonium hydroxide (25percent NH3). The solution was stirred for 24 h at rt.Thereafter, the mixture was concentrated in vacuo to yield a white solid that was used without further purification.
1 g	With ammonium hydroxide; In water; at 20 - 45℃; for 5.25h;	A 250-mL round-bottom flask was charged with 5.0 g of 10-bromodecanoic acid from Example 2 and 100 mL of ammonium hydroxide (28percent in water). The suspension was stirred at 20 °C for 3 hours. The suspension was heated to about 45 °C for 15 minutes. The mixture was then stirred at ambient temperature for 2 hours, then filtered. The filter cake was washed with water and 50percent isopropanol. The resulting solid was dried in vacuo to give a white powder (about 1 g). The chemical shifts for the NMR were as follows (relative to TMS): 1.35 (s, 10H), 1.63-1.70 (m, 4H), 2.05-2.07 (m, 2H), 2.36-2.40 (m, 2H), 3.03-3.07 (m, 2H), 1 1.75 (approx., s, 1H).

Reference： [1]Journal of the American Chemical Society,2009,vol. 131,p. 10610 - 10619
[2]Patent: WO2011/1419,2011,A1 .Location in patent: Page/Page column 19
[3]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 5054 - 5057
[4]Organic and Biomolecular Chemistry,2014,vol. 12,p. 8132 - 8137
[5]Patent: WO2018/80869,2018,A1 .Location in patent: Paragraph 0085

41
[ 13108-19-5 ]
[ 1175052-30-8 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 5054 - 5057

42
[ 13108-19-5 ]
C₂₃H₃₇NO₈ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 5054 - 5057

43
[ 13108-19-5 ]
(S)-10,12-dioxo-12-(2-oxotetrahydrofuran-3-ylamino)dodecan-1-ammonium trifluoroacetate [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 5054 - 5057

44
[ 13108-19-5 ]
(10-amino-1-hydroxydecylidene)bisphosphonic acid [ No CAS ]

Reference： [1]Molecules,2012,vol. 17,p. 10928 - 10945,18

45
[ 13108-19-5 ]
[ 50270-27-4 ]
4-chloro-2,6-bis(9-carboxynonylamino)pyrimidine-5-carbaldehyde [ No CAS ]