ChemFOnt: Showing chemical card for 2-Propene-1-sulfinothiocic-acids 2-propenyl ester (CFc000333189)

Record Information

Version

1.0

Creation Date

Update Date

2022-09-14 05:13:02 UTC

Chemfont ID

CFc000333189

Molecule Identification

Common Name

2-Propene-1-sulfinothiocic-acids 2-propenyl ester

Definition

Allicin, also known as allylthiosulfinate allyl ester or 2-propene-1-sulfinothioic acid s-2-propenyl ester, is a member of the class of compounds known as thiosulfinic acid esters. Thiosulfinic acid esters are organic compounds containing an ester of thiosulfinic acid with the general structure RS(=S)OR' (R, R'=alkyl, aryl). Allicin is slightly soluble (in water) and an extremely weak basic (essentially neutral) compound (based on its pKa). Allicin can be found in a number of food items such as chicory leaves, tea, watercress, and lemon thyme, which makes allicin a potential biomarker for the consumption of these food products. Allicin is an organosulfur compound obtained from garlic, a species in the family Alliaceae. It was first isolated and studied in the laboratory by Chester J. Cavallito and John Hays Bailey in 1944. When fresh garlic is chopped or crushed, the enzyme alliinase converts alliin into allicin, which is responsible for the aroma of fresh garlic. The allicin generated is unstable and quickly changes into a series of other sulfur-containing compounds such as diallyl disulfide. Allicin is part of a defense mechanism against attacks by pests on the garlic plant .

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-Propene-1-sulfinothioic acid S-2-propenyl ester	ChEBI
Thio-2-propene-1-sulfinic acid S-allyl ester	ChEBI
2-Propene-1-sulfinothioate S-2-propenyl ester	Generator
2-Propene-1-sulphinothioate S-2-propenyl ester	Generator
2-Propene-1-sulphinothioic acid S-2-propenyl ester	Generator
Thio-2-propene-1-sulfinate S-allyl ester	Generator
Thio-2-propene-1-sulphinate S-allyl ester	Generator
Thio-2-propene-1-sulphinic acid S-allyl ester	Generator
2-Propene-1-sulfinic acid, thio-, S-allyl ester	HMDB
2-Propene-1-sulfinothioic acid, S-2-propenyl ester	HMDB
2-Propene-1-sulfinothioic acid, S-2-propenyl ester (9ci)	HMDB
Allimin	HMDB, MeSH
Allitridi	HMDB
Allylthiosulfinate	HMDB, MeSH
Allylthiosulphinic acid allyl ester	HMDB
Dadso	HMDB
Diallyl disulfide-oxide	HMDB, MeSH
Diallyl thiosulfinate	HMDB
Diallyldisulfid-S-oxid	HMDB
S-2-Propenyl 2-propene-1-sulfinothioate, 9ci	HMDB
S-Allyl 2-propene-1-sulfinothioate	HMDB
S-Allyl acrylo-1-sulphinothioate	HMDB
S-Allyl prop-2-ene-1-sulfinothioate	HMDB
S-Prop-2-en-1-yl prop-2-ene-1-sulfinothioate	HMDB

Chemical Formula

C₆H₁₀OS₂

Average Molecular Weight

162.273

Monoisotopic Molecular Weight

162.017306322

IUPAC Name

3-[(prop-2-ene-1-sulfinyl)sulfanyl]prop-1-ene

Traditional Name

allicin

CAS Registry Number

539-86-6

SMILES

C=CCSS(=O)CC=C

InChI Identifier

InChI=1S/C6H10OS2/c1-3-5-8-9(7)6-4-2/h3-4H,1-2,5-6H2

InChI Key

JDLKFOPOAOFWQN-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as thiosulfinic acid esters. These are organic compounds containing an ester of thiosulfinic acid with the general structure RS(=S)OR' (R, R'=alkyl, aryl).

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Thiosulfinic acid esters

Sub Class

Not Available

Direct Parent

Thiosulfinic acid esters

Alternative Parents

Substituents

Thiosulfinic acid ester
Allyl sulfur compound
Sulfenyl compound
Sulfinyl compound
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organosulfur compound
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

sulfoxide (CHEBI:28411 )
botanical anti-fungal agent (CHEBI:28411 )
an organosulfur compound (CPD-9275 )

Functional Ontology

Not Available

Exogenous (HMDB: HMDB0033963)

Food

Herb and spice

Herb

Garlic (FooDB: FOOD00008)
Soft-necked garlic (FooDB: FOOD00850)

Process

Not Available

Role

Biological role

Anti septic (HMDB: HMDB0033963)

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	6.13 g/L	ALOGPS
logP	1.16	ALOGPS
logP	2.02	ChemAxon
logS	-1.4	ALOGPS
pKa (Strongest Basic)	-5.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	17.07 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	44.93 m³·mol⁻¹	ChemAxon
Polarizability	17.01 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon