Allithiamine

Chemical compound
  • None
Identifiers
  • N-[(4-Amino-2-methylpyrimidin-5-yl)methyl]-N-[(1Z)-4-hydroxy-1-methyl-2-(prop-2-en-1-yldisulfanyl)but-1-en-1-yl]formamide
CAS Number
  • 554-44-9 ☒N
PubChem CID
  • 3037212
ChemSpider
  • 2301021 checkY
UNII
  • 83SWN21920
Chemical and physical dataFormulaC15H22N4O2S2Molar mass354.49 g·mol−13D model (JSmol)
  • Interactive image
  • O=CN(/C(=C(\SSC\C=C)CCO)C)Cc1cnc(nc1N)C
InChI
  • InChI=1S/C15H22N4O2S2/c1-4-7-22-23-14(5-6-20)11(2)19(10-21)9-13-8-17-12(3)18-15(13)16/h4,8,10,20H,1,5-7,9H2,2-3H3,(H2,16,17,18)/b14-11- checkY
  • Key:WNCAVNGLACHSRZ-KAMYIIQDSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Allithiamine (thiamine allyl disulfide or TAD) is a lipid-soluble form of vitamin B1 which was discovered in garlic (Allium sativum) in the 1950s along with its homolog prosultiamine.[1] They were both investigated for their ability to treat Wernicke–Korsakoff syndrome and beriberi better than thiamine.[2]

See also

  • Vitamin B1 analogue

References

  1. ^ Fujiwara M, Watanabe H, Matsui K (1954). ""Allithiamine" A Newly Found Derivative of Vitamin B1". The Journal of Biochemistry. 41: 29–39. doi:10.1093/oxfordjournals.jbchem.a126421.
  2. ^ Rogers EF (April 1962). "Thiamine antagonists". Annals of the New York Academy of Sciences. 98 (2): 412–429. Bibcode:1962NYASA..98..412R. doi:10.1111/j.1749-6632.1962.tb30563.x. PMID 14493332. S2CID 32281714.
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Vitamins (A11)
Fat
soluble
A
D
E
K
  • Naphthoquinone
  • Phylloquinone (K1)#
  • Menaquinones (K2)
  • Menadione (K3)‡
  • Various (K4)
  • 4-Amino-2-methyl-1-naphthol (K5)‡
  • 2-Methylnaphthalene-1,4-diamine (K6)
  • 4-Amino-3-methyl-1-naphthol (K7)
Water
soluble
B
C
Combinations
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