4-(methylthio)-3-butenyl isothiocyanate profile

4-(methylthio)-3-butenyl isothiocyanate, also known as alliin, is a sulfur-containing compound found in garlic and other alliums. It is a potent antioxidant with potential anti-inflammatory and anti-cancer properties. Alliin is formed from the enzymatic breakdown of alliin, a precursor compound present in garlic. When garlic is crushed or cut, the enzyme alliinase converts alliin into alliin. Alliin is then readily converted to allicin, which is responsible for the pungent odor and flavor of garlic. Alliin has been studied for its potential health benefits, including its ability to lower blood pressure, improve cholesterol levels, and protect against heart disease and cancer. It is also believed to have antimicrobial and antifungal properties. However, more research is needed to fully understand the mechanisms and clinical efficacy of alliin.'
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4-(methylthio)-3-butenyl isothiocyanate: structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

ID Source	ID
PubMed CID	103500
MeSH ID	M0415529

Synonym
4-isothiocyanato-1-(methylsulfanyl)but-1-ene
51598-96-0
4-(methylthio)-3-butenyl isothiocyanate
4-isothiocyanato-1-(methylthio)-1-butene
4-(methylthio)-3-butenylisothiocyanate
DTXSID20965920

Excerpt	Reference	Relevance
" In contrast, some isothiocyanates (ITCs) have been reported to cause toxic effects, promotion activity, and/or carcinogenic potential in the urinary bladder of rats."	( Toxic effects of 4-methylthio-3-butenyl isothiocyanate (Raphasatin) in the rat urinary bladder without genotoxicity. Akagi, JI; Cho, YM; Hirata, T; Nakamura, T; Nakamura, Y; Nishikawa, A; Ogawa, K; Okamoto, S; Sasaki, A; Shirota, K; Suetome, N; Suzuki, I; Toyoda, T, 2017)	0.46

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	0 (0.00)	18.7374
1990's	0 (0.00)	18.2507
2000's	7 (38.89)	29.6817
2010's	11 (61.11)	24.3611
2020's	0 (0.00)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Publication Type	This drug (%)	All Drugs (%)
Trials	0 (0.00%)	5.53%
Reviews	0 (0.00%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	19 (100.00%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
1-anilino-8-naphthalenesulfonate 1-anilino-8-naphthalenesulfonate: RN given refers to parent cpd. 8-anilinonaphthalene-1-sulfonic acid : A naphthalenesulfonic acid that is naphthalene-1-sulfonic acid substituted by a phenylamino group at position 8.	2	1	aminonaphthalene; naphthalenesulfonic acid	fluorescent probe
sulforaphane sulforaphane: from Cardaria draba L.. sulforaphane : An isothiocyanate having a 4-(methylsulfinyl)butyl group attached to the nitrogen.	2.44	2	isothiocyanate; sulfoxide	antineoplastic agent; antioxidant; EC 3.5.1.98 (histone deacetylase) inhibitor; plant metabolite
diethanolamine diethanolamine: RN given refers to parent cpd. diethanolamine : A member of the class of ethanolamines that is ethanolamine having a N-hydroxyethyl substituent.	2	1	ethanolamines	human xenobiotic metabolite
catechin Catechin: An antioxidant flavonoid, occurring especially in woody plants as both (+)-catechin and (-)-epicatechin (cis) forms.. catechin : Members of the class of hydroxyflavan that have a flavan-3-ol skeleton and its substituted derivatives.. rac-catechin : A racemate comprising equimolar amounts of (+)- and (-)-catechin. (+)-catechin : The (+)-enantiomer of catechin and a polyphenolic antioxidant plant metabolite.	2.08	1	catechin	antioxidant; plant metabolite
nitrosobis(2-oxopropyl)amine nitrosobis(2-oxopropyl)amine: structure. nitrosobis(2-oxopropyl)amine : A nitrosamine that is iminodiacetone that is substituted by a nitroso group at the N-atom. It induces pancreatic ductal adenocarcinomas in Syrian golden hamsters (other rodents are not susceptible).	2.08	1	ketone; nitrosamine	carcinogenic agent
isothiocyanic acid [no description available]	2.02	1	hydracid; one-carbon compound
epigallocatechin gallate epigallocatechin gallate: a steroid 5alpha-reductase inhibitor and antimutagen in green tea (Camellia sinensis). (-)-epigallocatechin 3-gallate : A gallate ester obtained by the formal condensation of gallic acid with the (3R)-hydroxy group of (-)-epigallocatechin.	2.08	1	flavans; gallate ester; polyphenol	antineoplastic agent; antioxidant; apoptosis inducer; geroprotector; Hsp90 inhibitor; neuroprotective agent; plant metabolite
curcumin Curcumin: A yellow-orange dye obtained from tumeric, the powdered root of CURCUMA longa. It is used in the preparation of curcuma paper and the detection of boron. Curcumin appears to possess a spectrum of pharmacological properties, due primarily to its inhibitory effects on metabolic enzymes.. curcumin : A beta-diketone that is methane in which two of the hydrogens are substituted by feruloyl groups. A natural dyestuff found in the root of Curcuma longa.	2.08	1	aromatic ether; beta-diketone; diarylheptanoid; enone; polyphenol	anti-inflammatory agent; antifungal agent; antineoplastic agent; biological pigment; contraceptive drug; dye; EC 1.1.1.205 (IMP dehydrogenase) inhibitor; EC 1.1.1.21 (aldehyde reductase) inhibitor; EC 1.1.1.25 (shikimate dehydrogenase) inhibitor; EC 1.6.5.2 [NAD(P)H dehydrogenase (quinone)] inhibitor; EC 1.8.1.9 (thioredoxin reductase) inhibitor; EC 2.7.10.2 (non-specific protein-tyrosine kinase) inhibitor; EC 3.5.1.98 (histone deacetylase) inhibitor; flavouring agent; food colouring; geroprotector; hepatoprotective agent; immunomodulator; iron chelator; ligand; lipoxygenase inhibitor; metabolite; neuroprotective agent; nutraceutical; radical scavenger
1,1-diphenyl-2-picrylhydrazyl 1,1-diphenyl-2-picrylhydrazyl: A diphenyl picrate; the ability to decolorize this stable radical indicates reactivity of tested compounds (Banda, Anal Chem 46:1772-7 1974)	2.05	1
vitexin [no description available]	2.08	1	C-glycosyl compound; trihydroxyflavone	antineoplastic agent; EC 3.2.1.20 (alpha-glucosidase) inhibitor; plant metabolite; platelet aggregation inhibitor
apigenin Chamomile: Common name for several daisy-like plants (MATRICARIA; TRIPLEUROSPERMUM; ANTHEMIS; CHAMAEMELUM) native to Europe and Western Asia, now naturalized in the United States and Australia.	2.08	1	trihydroxyflavone	antineoplastic agent; metabolite
trovafloxacin glucoraphenin : A glucosinolic acid that consists of 1-thio-beta-D-glucopyranose attached to a 1-(methylsulfinyl)-5-[(sulfooxy)imino]pent-1-en-5-yl group at the anomeric sulfur.	2.06	1
zearalenone Zearalenone: (S-(E))-3,4,5,6,8,10-Hexahydro-14,16-dihydroxy-3-methyl-1H-2-benzoxacyclotetradecin-1,7(8H)-dione. One of a group of compounds known under the general designation of resorcylic acid lactones. Cis, trans, dextro and levo forms have been isolated from the fungus Gibberella zeae (formerly Fusarium graminearum). They have estrogenic activity, cause toxicity in livestock as feed contaminant, and have been used as anabolic or estrogen substitutes.. zearalenone : A macrolide comprising a fourteen-membered lactone fused to 1,3-dihydroxybenzene; a potent estrogenic metabolite produced by some Giberella species.	7.05	1	macrolide; resorcinols	fungal metabolite; mycoestrogen
sulphoraphene sulphoraphene: from radish; structure in first source	2.06	1
4-methylthio-3-butenyl glucosinolate 4-methylthio-3-butenyl glucosinolate: from Raphanus sativus sprouts; structure in first source	2.06	1
allopurinol Allopurinol: A XANTHINE OXIDASE inhibitor that decreases URIC ACID production. It also acts as an antimetabolite on some simpler organisms.. allopurinol : A bicyclic structure comprising a pyrazole ring fused to a hydroxy-substituted pyrimidine ring.	2.05	1	nucleobase analogue; organic heterobicyclic compound	antimetabolite; EC 1.17.3.2 (xanthine oxidase) inhibitor; gout suppressant; radical scavenger

Condition	Relationship Strength	Studies
Adenocarcinoma, Basal Cell [description not available]	2.52	2
Breast Cancer [description not available]	2.17	1
Adenocarcinoma A malignant epithelial tumor with a glandular organization.	2.52	2
Breast Neoplasms Tumors or cancer of the human BREAST.	2.17	1
Cancer of Esophagus [description not available]	2.21	1
Esophageal Neoplasms Tumors or cancer of the ESOPHAGUS.	2.21	1
Cancer of Colon [description not available]	2.08	1
Colonic Neoplasms Tumors or cancer of the COLON.	2.08	1
Bladder Diseases [description not available]	2.15	1
Cancer of Liver [description not available]	2.08	1
Liver Neoplasms Tumors or cancer of the LIVER.	2.08	1
Cancer of Pancreas [description not available]	2.08	1
Hyperplasia An increase in the number of cells in a tissue or organ without tumor formation. It differs from HYPERTROPHY, which is an increase in bulk without an increase in the number of cells.	2.08	1
Pancreatic Neoplasms Tumors or cancer of the PANCREAS. Depending on the types of ISLET CELLS present in the tumors, various hormones can be secreted: GLUCAGON from PANCREATIC ALPHA CELLS; INSULIN from PANCREATIC BETA CELLS; and SOMATOSTATIN from the SOMATOSTATIN-SECRETING CELLS. Most are malignant except the insulin-producing tumors (INSULINOMA).	2.08	1
Cell Transformation, Neoplastic Cell changes manifested by escape from control mechanisms, increased growth potential, alterations in the cell surface, karyotypic abnormalities, morphological and biochemical deviations from the norm, and other attributes conferring the ability to invade, metastasize, and kill.	2.02	1

4-(methylthio)-3-butenyl isothiocyanate

Description

Cross-References

Synonyms (6)

Research Excerpts

Toxicity

Research

Studies (18)

Market Indicators

Research Demand Index: 19.21

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