S-Allylcysteine

S-Allylcysteine (SAC) is an organosulfur compound that has the formula HO2CCH(NH2)CH2SCH2C=CH2. It is the S-allylated derivative of the amino acid cysteine. As such only the L-enantiomer is significant biologically. SAC constituent of aged garlic. A number of related compounds are found in garlic, including the disulfide S-"allylmercaptocysteine" (SAMC, HO2CCH(NH2)CH2SSCH2C=CH2) and γ-glutamyl-S-allylcysteine" (GSAC).[1]

S-Allyl cysteine
S-Allyl cysteine
S-Allyl cysteine
Names
IUPAC name
(R)-2-Amino-3-prop-2-enylsulfanylpropanoic acid
Other names
S-2-propenyl-L-cysteine; S-allyl-laevo-cysteine; S-allylcysteine
Identifiers
3D model (JSmol)
Abbreviations SAC
ChemSpider
ECHA InfoCard 100.166.686
UNII
  • InChI=1S/C6H11NO2S/c1-2-3-10-4-5(7)6(8)9/h2,5H,1,3-4,7H2,(H,8,9)/t5-/m0/s1 ☒N
    Key: ZFAHNWWNDFHPOH-YFKPBYRVSA-N ☒N
  • InChI=1/C6H11NO2S/c1-2-3-10-4-5(7)6(8)9/h2,5H,1,3-4,7H2,(H,8,9)/t5-/m0/s1
    Key: ZFAHNWWNDFHPOH-YFKPBYRVBL
  • O=C(O)[C@@H](N)CSC\C=C
Properties
C6H11NO2S
Molar mass 161.22 g/mol
Density 1.191 ± 0.06 g/cm3
Melting point 219 to 220 °C (426 to 428 °F; 492 to 493 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Allylcysteine is of interest for its potential medicinal properties.[2] and as a chemopreventive.[3]

See also
  • Alliin, the S-oxide of allyl cysteine

References
  1. Fujii, Takuto; Matsutomo, Toshiaki; Kodera, Yukihiro (2018). "Changes of S-Allylmercaptocysteine and γ-Glutamyl-S-allylmercaptocysteine Contents and Their Putative Production Mechanisms in Garlic Extract during the Aging Process". Journal of Agricultural and Food Chemistry. 66 (40): 10506–10512. doi:10.1021/acs.jafc.8b02541. PMID 30226990. S2CID 52297055.
  2. Yeh YY, Liu L (2001). "Cholesterol-lowering effect of garlic extracts and organosulfur compounds: human and animal studies". Journal of Nutrition. 131 (3s): 989S–93S. doi:10.1093/jn/131.3.989S. PMID 11238803.
  3. Arora, Annu; Tripathi, Chitra; Shukla, Yogeshwer (2005). "Garlic and its organosulfides as potential chemopreventive agents: a review". Current Cancer Therapy Reviews. 1 (2): 199–205. doi:10.2174/1573394054021772.
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