(Z)-ajoene
(Z)-1-(prop-2-enyldisulfanyl)-3-prop-2-enylsulfinylprop-1-ene
 
Notes:
None found
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CAS Number: 92285-00-2Picture of molecule3D/inchi
FDA UNII: J9XLK7547H
Nikkaji Web: J2.217.932B
XlogP3-AA: 1.70 (est)
Molecular Weight: 234.40478000
Formula: C9 H14 O S3
BioActivity Summary: listing
NMR Predictor: Predict (works with chrome or firefox)
Category: natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
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Physical Properties:
Assay: 95.00 to 100.00 % 
Food Chemicals Codex Listed: No
Flash Point: 32.00 °F. TCC ( 0.00 °C. ) (est)
Soluble in:
 water, 3.441 mg/L @ 25 °C (est)
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Organoleptic Properties:
 
Odor and/or flavor descriptions from others (if found).
 
 
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Cosmetic Information:
None found
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Suppliers:
 None found
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Safety Information:
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
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Safety in Use Information:
Category: natural substances and extractives
Recommendation for (Z)-ajoene usage levels up to:
 not for fragrance use.
 
Recommendation for (Z)-ajoene flavor usage levels up to:
 not for flavor use.
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Safety References:
EPI System: View
AIDS Citations: Search
Cancer Citations: Search
Toxicology Citations: Search
EPA ACToR: Toxicology Data
EPA Substance Registry Services (SRS): Registry
Laboratory Chemical Safety Summary : 9881148
National Institute of Allergy and Infectious Diseases: Data
 (Z)-1-(prop-2-enyldisulfanyl)-3-prop-2-enylsulfinylprop-1-ene
Chemidplus: 0092285002
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References:
 (Z)-1-(prop-2-enyldisulfanyl)-3-prop-2-enylsulfinylprop-1-ene
NIST Chemistry WebBook: Search Inchi
Pubchem (cid): 9881148
Pubchem (sid): 172649019
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Other Information:
(IUPAC): Atomic Weights of the Elements 2011 (pdf)
Videos: The Periodic Table of Videos
tgsc: Atomic Weights use for this web site
(IUPAC): Periodic Table of the Elements
CHEBI: View
CHEMBL: View
KEGG (GenomeNet): C16757
HMDB (The Human Metabolome Database): Search
VCF-Online: VCF Volatile Compounds in Food
ChemSpider: View
Wikipedia: View
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Potential Blenders and core components note
 
None Found
 
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Potential Uses:
None Found
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Occurrence (nature, food, other): note
 garlic
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Synonyms:
(Z)-1-(prop-2-enyldisulfanyl)-3-prop-2-enylsulfinylprop-1-ene
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Articles:
PubMed: Development of garlic bioactive compounds analytical methodology based on liquid phase microextraction using response surface design. Implications for dual analysis: Cooked and biological fluids samples.
PubMed: Chemical composition and bioactive compounds of garlic (Allium sativum L.) as affected by pre- and post-harvest conditions: A review.
PubMed: The redox-active drug metronidazole and thiol-depleting garlic compounds act synergistically in the protist parasite Spironucleus vortens.
PubMed: The garlic compound ajoene targets protein folding in the endoplasmic reticulum of cancer cells.
PubMed: Optimizing conditions for E-and Z-ajoene formation from garlic juice using response surface methodology.
PubMed: Applications of thin-layer chromatography in extraction and characterisation of ajoene from garlic bulbs.
PubMed: Systemic approaches identify a garlic-derived chemical, Z-ajoene, as a glioblastoma multiforme cancer stem cell-specific targeting agent.
PubMed: Neuroprotective effects of Z-ajoene, an organosulfur compound derived from oil-macerated garlic, in the gerbil hippocampal CA1 region after transient forebrain ischemia.
PubMed: Solid phase microextraction coupled to liquid chromatography. Analysis of organosulphur compounds avoiding artifacts formation.
PubMed: Application of the DataChip/MetaChip technology for the evaluation of ajoene toxicity in vitro.
PubMed: Transformation of synthetic allicin: the influence of ultrasound, microwaves, different solvents and temperatures, and the products isolation.
PubMed: Structure-activity studies on the anti-proliferation activity of ajoene analogues in WHCO1 oesophageal cancer cells.
PubMed: Anti-proliferation activity of synthetic ajoene analogues on cancer cell-lines.
PubMed: Activities of Z-ajoene against tumour and viral spreading in vitro.
PubMed: [Characteristics of uptake, transport and efflux of Z- and E-ajoenes in Caco-2 cell monolayers in vitro].
PubMed: [Z-ajoene causes cell cycle arrest at G2/M and decrease of telomerase activity in HL-60 cells].
PubMed: Bioactive S-alk(en)yl cysteine sulfoxide metabolites in the genus Allium: the chemistry of potential therapeutic agents.
PubMed: Improvement of scopolamine-induced memory impairment by Z-ajoene in the water maze in mice.
PubMed: Z-ajoene induces apoptosis of HL-60 cells: involvement of Bcl-2 cleavage.
PubMed: Antitumor activity of Z-ajoene, a natural compound purified from garlic: antimitotic and microtubule-interaction properties.
PubMed: An organosulfur compound isolated from oil-macerated garlic extract, and its antimicrobial effect.
PubMed: Ajoene is an inhibitor and subversive substrate of human glutathione reductase and Trypanosoma cruzi trypanothione reductase: crystallographic, kinetic, and spectroscopic studies.
PubMed: Antimicrobial activity of a compound isolated from an oil-macerated garlic extract.
PubMed: Identification and HPLC quantitation of the sulfides and dialk(en)yl thiosulfinates in commercial garlic products.
PubMed: Products of Allicin Transformation: Ajoenes and Dithiins, Characterization and their Determination by HPLC*.
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