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allithiamine

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allithiamine

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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. They were both investigated for their ability to treat Wernicke–Korsakoff syndrome and beriberi better than thiamine.

Chemical data

Formula
C15H22N4O2S2
Molecular weight
354.5 g/mol
IUPAC name
N-[(4-amino-2-methylpyrimidin-5-yl)methyl]-N-[(Z)-5-hydroxy-3-(prop-2-enyldisulfanyl)pent-2-en-2-yl]formamide
SMILES
CC1=NC=C(C(=N1)N)CN(C=O)/C(=C(/CCO)\SSCC=C)/C
InChIKey
WNCAVNGLACHSRZ-KAMYIIQDSA-N
XLogP
0.9
Polar surface area
143 Ų
H-bond donors
2
H-bond acceptors
7
Formal charge
0

via PubChem

Wikidata facts

Mass
354.118
Show 4 more facts
chemical formula
C₁₅H₂₂N₄O₂S₂
canonical SMILES
CC1=NC=C(C(=N1)N)CN(C=O)C(=C(CCO)SSCC=C)C
isomeric SMILES
CC1=NC=C(C(=N1)N)CN(C=O)/C(=C(/CCO)\SSCC=C)/C
Commons category
Allithiamine
Sources (1)

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Encyclopedic overview

2 sections
Contents
  • See also
  • References

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. They were both investigated for their ability to treat Wernicke–Korsakoff syndrome and beriberi better than thiamine.

== See also == Vitamin B1 analogue

Excerpted from Wikipedia’s “allithiamine” article, available under the CC BY-SA 4.0 licence.

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