ChemicalBook--->CAS DataBase List--->135304-07-3

135304-07-3

135304-07-3 Structure

135304-07-3 Structure
IdentificationBack Directory
[Name]

AFC
[CAS]

135304-07-3
[Synonyms]

AFC
AFC USP/EP/BP
AC-CYS(FARNESYL)-OH
Ac-L-Cys(Farnesyl)-OH
AC-CYSTEINE(FARNESYL)-OH
n-acetyl-s-farnesylcysteine
N-Acetyl-L-farnesylcysteine
ACETYL-S-FARNESYL-L-CYSTEINE
N-ACETYL-S-FARNESYL-L-CYSTEINE
N-ALPHA-ACETYL-S-FARNESYL-L-CYSTEINE
N-Acetyl-S-farnesyl-L-cysteine (AFC)
Acetyl-S-farnesyl-L-cysteine≥ 99% (TLC)
N-Acetyl-S-trans,trans-farnesyl-L-cysteine
N-Acetyl-S-(3,7,11-trimethyl-2ε,6ε,10-dodecatrienyl)-L-cysteine
N-ACETYL-S-(3,7,11-TRIMETHYL-2E,6E,10-DODECATRIENYL)-L-CYSTEINE
L-Cysteine,N-acetyl-S-[(2E,6E)-3,7,11-trimethyl-2,6,10-dodecatrien-1-yl]-
(R)-2-acetamido-3-((2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienylthio) propanoic acid
[Molecular Formula]

C20H33NO3S
[MDL Number]

MFCD00871540
[MOL File]

135304-07-3.mol
[Molecular Weight]

367.55
Chemical PropertiesBack Directory
[Boiling point ]

566.1±50.0 °C(Predicted)
[density ]

1.038±0.06 g/cm3(Predicted)
[storage temp. ]

-15°C
[solubility ]

Soluble in DMSO (up to 25 mg/ml) or in Ethanol (up to 25 mg/ml)
[form ]

Pale yellow oil.
[pka]

3.31±0.10(Predicted)
[color ]

Yellow
[Stability:]

Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 3 months.
[Cosmetics Ingredients Functions]

SKIN CONDITIONING
REDUCING
[LogP]

5.860 (est)
Safety DataBack Directory
[HazardClass ]

IRRITANT
Hazard InformationBack Directory
[Description]

N-acetyl-S-farnesyl-L-Cysteine is a synthetic substrate for the isoprenylated protein methyltransferase (also known as S-adenosylmethionine-dependent methyltransferase). Because it is able to serve as a substrate for the methyltransferase, it effectively functions as an inhibitor of methylation of endogenous isoprenylated proteins.
[Chemical Properties]

Yellow-red oil
[Uses]

Arazine is an FTS (trans-Farnesylthiosalicylic Acid) compound, which does not inhibit EJ cell growth and does not affect Ras.
[Definition]

ChEBI: Acetyl-farnesyl-cysteine is a sesquiterpenoid.
[in vivo]

Arazine (AFC) (2,000?μg/20?μl; applied on ear) produces a dose-dependent inhibition of the TPA-induced edema, with the maximal reduction of edema approaching 73%, with a 50% effective dose (ED50) of 55±12?μg/20?μl[1].

Animal Model:TPA-induced ear acute inflammation in mouse[1]
Dosage:2000?μg/20?μl
Administration:2000?μg/20?μl; Applied on ear
Result:Inhibited ear edema, as measured by ear weight.
[References]

1) Volker?et al.?(1991),?Effects of farnesylcyteine analogs on protein carboxyl methylation and signal transduction; J. Biol. Chem.?266?21515 2) Xu?et al.?(1996),?Inhibition of capacitative Ca2+ entry into cells by farnesyl analogs; Mol. Pharmacol.?50?1495 3) Rosado and Sage (2000),?Farnesylcyteine analogues inhibit store-regulated Ca2+ entry in human platelets: evidence for involvement of small GTP-binding proteins and actin cytoskeleton; Biochem. J.?347?183 4) Gordon?et al.?(2008),?Topical N-acetyl-S-farnesyl-L-cysteine inhibits mouse skin inflammation, and unlike dexamethasone, its effects are restricted to the application site; J. Invest. Dermatol.?128?643 5) Adhami?et al.?(2012),?N-acetyl-S-farnesyl-L-cysteine suppresses chemokine production by human dermal microvascular endothelial cells;?Exp. Dermatol.?21?700
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