jacaranone
2,5-cyclohexadiene-1-acetic acid, 1-hydroxy-4-oxo-, methyl ester
Identification
| Name | jacaranone |
| IUPAC | methyl 2-(1-hydroxy-4-oxocyclohexa-2,5-dien-1-yl)acetate |
| CAS Number | 60263-07-2 |
| FDA UNII | Search |
| Molecular Formula | C9 H10 O4 |
| Molecular Weight | 182.17550000 |
| Nikkaji Number | J601.244B |
Regulatory
Physical Properties
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Boiling Point | 327.10 °C. @ 760.00 mm Hg (est) |
| Flash Point | 271.00 °F. TCC ( 132.50 °C. ) (est) |
| logP (o/w) | -0.250 (est) |
| Soluble in | water, 5.227e+005 mg/L @ 25 °C (est) |
No sensory data available
Safety Information
| Oral/Parenteral Toxicity | Not determined |
| Dermal Toxicity | Not determined |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements']
Safety in Use
| Category | natural substances and extractives |
| Recommendation for jacaranone usage levels up to | not for fragrance use. |
| Recommendation for jacaranone flavor usage levels up to | not for flavor use. |
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Potential Uses
Natural Occurrence
Synonyms
2,5-
cyclohexadiene-1-acetic acid, 1-hydroxy-4-oxo-, methyl ester
1-
hydroxy-4-oxo-2,5-cyclohexadiene-1-acetic acid methyl ester
jacaramome
methyl (1-hydroxy-4-oxo-2,5-cyclohexadien-1-yl)acetate
methyl (1-hydroxy-4-oxocyclohexa-2,5-dien-1-yl)acetate
methyl 2-(1-hydroxy-4-oxocyclohexa-2,5-dien-1-yl)acetate
methyl-1-hydroxy-4-oxo-2,5-chclohexadiene-1-acetate
PubMed:
Two new glycosides from the fruits of Forsythia suspense.
PubMed:
A new phenylethanoid glucoside from Jacaranda mimosifolia.
PubMed:
Jacaranone induces apoptosis in melanoma cells via ROS-mediated downregulation of Akt and p38 MAPK activation and displays antitumor activity in vivo.
PubMed:
Differential tissue distribution of metabolites in Jacobaea vulgaris, Jacobaea aquatica and their crosses.
PubMed:
Authentication of Senecio scandens and S. vulgaris based on the comprehensive secondary metabolic patterns gained by UPLC-DAD/ESI-MS.
PubMed:
Anti-malarial, anti-trypanosomal, and anti-leishmanial activities of jacaranone isolated from Pentacalia desiderabilis (Vell.) Cuatrec. (Asteraceae).
PubMed:
[Chemical constituents from Aster sampsonii].
PubMed:
Jacaranone-derived glucosidic esters from Jacaranda glabra and their activity against Plasmodium falciparum.
PubMed:
A new jacaranone derivative from Senecio scandens var. incisus.
PubMed:
Isolation of jacaranone, a sedative constituent extracted from the flowers of the Mexican tree Ternstroemia pringlei.
PubMed:
Fast counter current chromatography of n-butanolic fraction from Senecio giganteus (Asteraceae).
PubMed:
Jacaranone analogs from Senecio scandens.
PubMed:
NMR metabolomics of thrips (Frankliniella occidentalis) resistance in Senecio hybrids.
PubMed:
Jacaranda--an ethnopharmacological and phytochemical review.
PubMed:
A new compound from Senecio cannabifolius var integrilifolius.
PubMed:
Jacaranone: a cytotoxic constituent from Senecio ambiguus subsp. ambiguus (biv.) DC. against renal adenocarcinoma ACHN and prostate carcinoma LNCaP cells.
PubMed:
Jacaranone glycosides from Senecio scandens.
PubMed:
Jacaranone and related compounds from the fresh fruits of Ternstroemia japonica and their antioxidative activity.
PubMed:
In-vitro antiproliferative effects on human tumour cell lines of extracts and jacaranone from Senecio leucanthemifolius Poiret.
PubMed:
Insecticides in Chinese medicinal plants: survey leading to jacaranone, a neurotoxicant and glutathione-reactive quinol.
PubMed:
Secondary metabolites from Senecio minutus and Senecio boissieri: a new jacaranone derivative.
PubMed:
Synthesis of naphthoquinoles as potential antitumor agents related to jacaranone.
PubMed:
Potential anticancer agents. IV. Constituents of Jacaranda caucana Pittier (Bignoniaceae).
PubMed:
Potential anticancer agents. III. Jacaranone, a novel phytoquinoid from Jacaranda caucana.