Product Name

  • Name

    N-Acetyl-S-trans,trans-farnesyl-L-cysteine

  • EINECS
  • CAS No. 135304-07-3
  • Article Data4
  • CAS DataBase
  • Density 1.038 g/cm3
  • Solubility
  • Melting Point
  • Formula C20H33NO3S
  • Boiling Point 566.1 °C at 760 mmHg
  • Molecular Weight 367.553
  • Flash Point 296.1 °C
  • Transport Information
  • Appearance
  • Safety
  • Risk Codes
  • Molecular Structure Molecular Structure of 135304-07-3 (N-Acetyl-S-trans,trans-farnesyl-L-cysteine)
  • Hazard Symbols
  • Synonyms N-acetyl-S-farnesylcysteine;N-acetyl-S-trans, trans-farnesyl-L-cysteine;N-acetylfarnesylcysteine;N-AFC
  • PSA 91.70000
  • LogP 5.11900

Synthetic route

N-acetylcystein
616-91-1

N-acetylcystein

farnesyl bromide
24163-93-7, 24163-94-8, 56881-57-3, 6874-67-5, 28290-41-7

farnesyl bromide

N-acetyl-S-trans,trans-farnesyl-L-cysteine
135304-07-3

N-acetyl-S-trans,trans-farnesyl-L-cysteine

Conditions
ConditionsYield
With ammonia In methanol for 16h;99%
With ammonia In methanol Alkylation;
N-acetyl cysteine (S-farnesyl) methyl ester
135304-08-4

N-acetyl cysteine (S-farnesyl) methyl ester

N-acetyl-S-trans,trans-farnesyl-L-cysteine
135304-07-3

N-acetyl-S-trans,trans-farnesyl-L-cysteine

Conditions
ConditionsYield
With lithium hydroxide In methanol; water for 24h;84%
trans,trans-farnesyl-L-cysteine
68000-92-0

trans,trans-farnesyl-L-cysteine

acetic anhydride
108-24-7

acetic anhydride

N-acetyl-S-trans,trans-farnesyl-L-cysteine
135304-07-3

N-acetyl-S-trans,trans-farnesyl-L-cysteine

Conditions
ConditionsYield
With sodium hydroxide at 0 - 20℃;52%
Farnesol
106-28-5

Farnesol

N-acetyl-S-trans,trans-farnesyl-L-cysteine
135304-07-3

N-acetyl-S-trans,trans-farnesyl-L-cysteine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: polymer supported PPh3; CBr4 / CH2Cl2 / 5 h
2: 70 percent / zinc acetate; TFA / dimethylformamide; acetonitrile; H2O / 24 h
3: 84 percent / LiOH / methanol; H2O / 24 h
View Scheme
farnesyl bromide
24163-93-7, 24163-94-8, 56881-57-3, 6874-67-5, 28290-41-7

farnesyl bromide

N-acetyl-S-trans,trans-farnesyl-L-cysteine
135304-07-3

N-acetyl-S-trans,trans-farnesyl-L-cysteine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 70 percent / zinc acetate; TFA / dimethylformamide; acetonitrile; H2O / 24 h
2: 84 percent / LiOH / methanol; H2O / 24 h
View Scheme
N-acetyl-S-trans,trans-farnesyl-L-cysteine
135304-07-3

N-acetyl-S-trans,trans-farnesyl-L-cysteine

titanium (R)-2-acetamido-3-((2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienylthio)propanoate

titanium (R)-2-acetamido-3-((2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienylthio)propanoate

Conditions
ConditionsYield
Stage #1: N-acetyl-S-trans,trans-farnesyl-L-cysteine With sodium hydroxide In water
Stage #2: With titanium tetrachloride In tetrahydrofuran at 20℃;		91%
N-acetyl-S-trans,trans-farnesyl-L-cysteine
135304-07-3

N-acetyl-S-trans,trans-farnesyl-L-cysteine

silver (R)-2-acetamido-3-((2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienylthio)propanoate

silver (R)-2-acetamido-3-((2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienylthio)propanoate

Conditions
ConditionsYield
Stage #1: N-acetyl-S-trans,trans-farnesyl-L-cysteine With sodium hydroxide In water at 20℃; for 0.166667h;
Stage #2: With silver nitrate In water for 1h;		84%
N-acetyl-S-trans,trans-farnesyl-L-cysteine
135304-07-3

N-acetyl-S-trans,trans-farnesyl-L-cysteine

C20H35N3O2S
1160502-59-9

C20H35N3O2S

Conditions
ConditionsYield
Stage #1: N-acetyl-S-trans,trans-farnesyl-L-cysteine In dichloromethane for 0.5h;
Stage #2: With hydrazine In tetrahydrofuran; dichloromethane at 20℃; for 3h;		80%
D-(+)-glucosamine hydrochloride
66-84-2

D-(+)-glucosamine hydrochloride

N-acetyl-S-trans,trans-farnesyl-L-cysteine
135304-07-3

N-acetyl-S-trans,trans-farnesyl-L-cysteine

glucosamine (R)-2-amino-3-((2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienylthio)propanoate

glucosamine (R)-2-amino-3-((2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienylthio)propanoate

Conditions
ConditionsYield
Stage #1: N-acetyl-S-trans,trans-farnesyl-L-cysteine With sodium hydroxide In ethanol; water
Stage #2: D-(+)-glucosamine hydrochloride In ethanol; water for 0.5h;		76%
N-acetyl-S-trans,trans-farnesyl-L-cysteine
135304-07-3

N-acetyl-S-trans,trans-farnesyl-L-cysteine

phenylhydrazine
100-63-0

phenylhydrazine

C26H39N3O2S
1160502-64-6

C26H39N3O2S

Conditions
ConditionsYield
Stage #1: N-acetyl-S-trans,trans-farnesyl-L-cysteine With triethylamine; HATU In tetrahydrofuran for 0.5h;
Stage #2: phenylhydrazine In tetrahydrofuran		73%
N-acetyl-S-trans,trans-farnesyl-L-cysteine
135304-07-3

N-acetyl-S-trans,trans-farnesyl-L-cysteine

zinc (R)-2-acetamido-3-((2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienylthio)propanoate

zinc (R)-2-acetamido-3-((2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienylthio)propanoate

Conditions
ConditionsYield
Stage #1: N-acetyl-S-trans,trans-farnesyl-L-cysteine With sodium hydroxide In water at 20℃; for 0.166667h;
Stage #2: With zinc(II) chloride In water for 1h;		67%
N-acetyl-S-trans,trans-farnesyl-L-cysteine
135304-07-3

N-acetyl-S-trans,trans-farnesyl-L-cysteine

methylhydrazine
60-34-4

methylhydrazine

C21H37N3O2S
1160502-63-5

C21H37N3O2S

Conditions
ConditionsYield
Stage #1: N-acetyl-S-trans,trans-farnesyl-L-cysteine With triethylamine; HATU In tetrahydrofuran for 0.5h;
Stage #2: methylhydrazine In tetrahydrofuran		65%
N-acetyl-S-trans,trans-farnesyl-L-cysteine
135304-07-3

N-acetyl-S-trans,trans-farnesyl-L-cysteine

strontium (R)-2-acetamido-3-((2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienylthio)propanoate

strontium (R)-2-acetamido-3-((2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienylthio)propanoate

Conditions
ConditionsYield
Stage #1: N-acetyl-S-trans,trans-farnesyl-L-cysteine With sodium hydroxide In water
Stage #2: With strontium chloride In water		57%
N-acetyl-S-trans,trans-farnesyl-L-cysteine
135304-07-3

N-acetyl-S-trans,trans-farnesyl-L-cysteine

C20H34N2O3S
1160502-62-4

C20H34N2O3S

Conditions
ConditionsYield
Stage #1: N-acetyl-S-trans,trans-farnesyl-L-cysteine In dichloromethane for 0.5h;
Stage #2: With hydroxylamine In tetrahydrofuran; dichloromethane; water at 20℃; for 3h;		45%
N-acetyl-S-trans,trans-farnesyl-L-cysteine
135304-07-3

N-acetyl-S-trans,trans-farnesyl-L-cysteine

acetic acid hydrazide
1068-57-1

acetic acid hydrazide

C22H37N3O3S
1160502-65-7

C22H37N3O3S

Conditions
ConditionsYield
Stage #1: N-acetyl-S-trans,trans-farnesyl-L-cysteine With triethylamine; HATU In tetrahydrofuran for 0.5h;
Stage #2: acetic acid hydrazide In tetrahydrofuran		35%
nicotinamide hydrochloride
25334-23-0

nicotinamide hydrochloride

N-acetyl-S-trans,trans-farnesyl-L-cysteine
135304-07-3

N-acetyl-S-trans,trans-farnesyl-L-cysteine

nicotinamide (R)-2-acetamido-3-((2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienylthio)propanoate
1239578-25-6

nicotinamide (R)-2-acetamido-3-((2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienylthio)propanoate

Conditions
ConditionsYield
Stage #1: N-acetyl-S-trans,trans-farnesyl-L-cysteine With sodium hydroxide In water
Stage #2: nicotinamide hydrochloride In ethanol for 1h;		35%
(R)-Phenylglycinol
56613-80-0

(R)-Phenylglycinol

N-acetyl-S-trans,trans-farnesyl-L-cysteine
135304-07-3

N-acetyl-S-trans,trans-farnesyl-L-cysteine

N-acetyl-S-farnesyl-L-cysteine-(D)-α-phenylglycinolamide

N-acetyl-S-farnesyl-L-cysteine-(D)-α-phenylglycinolamide

Conditions
ConditionsYield
With 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 0 - 20℃;
N-acetyl-S-trans,trans-farnesyl-L-cysteine
135304-07-3

N-acetyl-S-trans,trans-farnesyl-L-cysteine

isobutyl chloroformate
543-27-1

isobutyl chloroformate

C25H41NO5S

C25H41NO5S

Conditions
ConditionsYield
With 4-methyl-morpholine In tetrahydrofuran at -15℃; Acetylation;
N-acetyl-S-trans,trans-farnesyl-L-cysteine
135304-07-3

N-acetyl-S-trans,trans-farnesyl-L-cysteine

N-[(R)-3-Diazo-2-oxo-1-((2E,6E)-3,7,11-trimethyl-dodeca-2,6,10-trienylsulfanylmethyl)-propyl]-acetamide
253871-52-2

N-[(R)-3-Diazo-2-oxo-1-((2E,6E)-3,7,11-trimethyl-dodeca-2,6,10-trienylsulfanylmethyl)-propyl]-acetamide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: NMM / tetrahydrofuran / -15 °C
2: diethyl ether / 0 °C
View Scheme
N-acetyl-S-trans,trans-farnesyl-L-cysteine
135304-07-3

N-acetyl-S-trans,trans-farnesyl-L-cysteine

N-[(R)-3-Chloro-2-oxo-1-((2E,6E)-3,7,11-trimethyl-dodeca-2,6,10-trienylsulfanylmethyl)-propyl]-acetamide

N-[(R)-3-Chloro-2-oxo-1-((2E,6E)-3,7,11-trimethyl-dodeca-2,6,10-trienylsulfanylmethyl)-propyl]-acetamide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: NMM / tetrahydrofuran / -15 °C
2: diethyl ether / 0 °C
3: HCl / ethyl acetate / 0.17 h / 0 °C
View Scheme

L-Cysteine,N-acetyl-S-[(2E,6E)-3,7,11-trimethyl-2,6,10-dodecatrien-1-yl]- Specification

The L-Cysteine,N-acetyl-S-[(2E,6E)-3,7,11-trimethyl-2,6,10-dodecatrien-1-yl]-, with the CAS registry number of 135304-07-3, is also known as N-Acetylfarnesylcysteine. This chemical's molecular formula is C20H33NO3S and molecular weight is 367.55. What's more, its IUPAC name is (2R)-2-Acetamido-3-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienyl]sulfanylpropanoic acid. In addition, it must be stored in airtight containers. It can inhibit Prenyl-cysteine carboxyl methyl transferases.

Physical properties about the L-Cysteine,N-acetyl-S-[(2E,6E)-3,7,11-trimethyl-2,6,10-dodecatrien-1-yl]- are: (1)ACD/LogP: 5.86; (2)# of Rule of 5 Violations: 1; (3)ACD/LogD (pH 5.5): 3.34; (4)ACD/LogD (pH 7.4): 2.19; (5)ACD/BCF (pH 5.5): 50.5; (6)ACD/BCF (pH 7.4): 3.56; (7)ACD/KOC (pH 5.5): 111.01; (8)ACD/KOC (pH 7.4): 7.82; (9)#H bond acceptors: 4; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 12; (12)Polar Surface Area: 71.91 Å2; (13)Index of Refraction: 1.519; (14)Molar Refractivity: 107.55 cm3; (15)Molar Volume: 353.8 cm3; (16)Surface Tension: 38.4 dyne/cm; (17)Density: 1.038 g/cm3; (18)Flash Point: 296.1 °C; (19)Enthalpy of Vaporization: 92.91 kJ/mol; (20)Boiling Point: 566.1 °C at 760 mmHg; (21)Vapour Pressure: 2.71E-14 mmHg at 25 °C.

You can still convert the following datas into molecular structure:
(1) SMILES: O=C(N[C@H](C(=O)O)CSC\C=C(/C)CC\C=C(/C)CC\C=C(/C)C)C
(2) InChI: InChI=1/C20H33NO3S/c1-15(2)8-6-9-16(3)10-7-11-17(4)12-13-25-14-19(20(23)24)21-18(5)22/h8,10,12,19H,6-7,9,11,13-14H2,1-5H3,(H,21,22)(H,23,24)/b16-10+,17-12+/t19-/m0/s1
(3) InChIKey: XTURYZYJYQRJDO-BNAHBJSTBA

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