| Identification | Back 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 Properties | Back 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) |
| Hazard Information | Back 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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