xanthoangelol
2',4,4'-trihydroxy-3'-geranylchalcone
Identification
| Name | xanthoangelol |
| IUPAC | (E)-1-[3-[(2E)-3,7-dimethylocta-2,6-dienyl]-2,4-dihydroxyphenyl]-3-(4-hydroxyphenyl)prop-2-en-1-one |
| CAS Number | 62949-76-2 |
| FDA UNII | 91D4GN26Z1 |
| Molecular Formula | C25 H28 O4 |
| Molecular Weight | 392.49496000 |
| Nikkaji Number | J20.204E |
Regulatory
Physical Properties
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Boiling Point | 605.80 °C. @ 760.00 mm Hg (est) |
| Flash Point | 634.00 °F. TCC ( 334.20 °C. ) (est) |
| logP (o/w) | 7.240 (est) |
| Soluble in | water, 0.003845 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 xanthoangelol usage levels up to | not for fragrance use. |
| Recommendation for xanthoangelol flavor usage levels up to | not for flavor use. |
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Potential Uses
Natural Occurrence
Synonyms
(E,E)-1-(3-(3,7-
dimethyl-2,6-octadienyl)-2,4-dihydroxyphenyl)-3-(4-hydroxyphenyl)-2-propen-1-one
2-
propen-1-one, 1-[3-[(2E)-3,7-dimethyl-2,6-octadienyl]-2,4-dihydroxyphenyl]-3-(4-hydroxyphenyl)-, (2E)-
2',4,4'-
trihydroxy-3'-geranylchalcone
PubMed:
Bioassay-guided isolation and identification of anti-platelet-active compounds from the root of Ashitaba (Angelica keiskei Koidz.).
PubMed:
Chalcones suppress fatty acid-induced lipid accumulation through a LKB1/AMPK signaling pathway in HepG2 cells.
PubMed:
Quantitative analysis of phenolic metabolites from different parts of Angelica keiskei by HPLC-ESI MS/MS and their xanthine oxidase inhibition.
PubMed:
Inhibitory Effects of 4-Hydroxyderricin and Xanthoangelol on Lipopolysaccharide-Induced Inflammatory Responses in RAW264 Macrophages.
PubMed:
Xanthoangelol and 4-Hydroxyderricin Are the Major Active Principles of the Inhibitory Activities against Monoamine Oxidases on Angelica keiskei K.
PubMed:
Compounds isolated from Psoralea corylifolia seeds inhibit protein kinase activity and induce apoptotic cell death in mammalian cells.
PubMed:
4-Hydroxyderricin and xanthoangelol from Ashitaba (Angelica keiskei) suppress differentiation of preadiopocytes to adipocytes via AMPK and MAPK pathways.
PubMed:
The inhibitory effects of representative chalcones contained in Angelica keiskei on melanin biosynthesis in B16 melanoma cells.
PubMed:
Six new chalcones from Angelica keiskei inducing adiponectin production in 3T3-L1 adipocytes.
PubMed:
Absorption and metabolism of 4-hydroxyderricin and xanthoangelol after oral administration of Angelica keiskei (Ashitaba) extract in mice.
PubMed:
Application of mixture analysis to crude materials from natural resources (III): NMR spectral studies to analyze chalcones from Angelica keiskei.
PubMed:
Cytotoxic activities and anti-tumor-promoting effects of microbial transformation products of prenylated chalcones from Angelica keiskei.
PubMed:
Xanthoangelols isolated from Angelica keiskei inhibit inflammatory-induced plasminogen activator inhibitor 1 (PAI-1) production.
PubMed:
The role of chalcones in suppression of NF-κB-mediated inflammation and cancer.
PubMed:
Prenylated chalcones 4-hydroxyderricin and xanthoangelol stimulate glucose uptake in skeletal muscle cells by inducing GLUT4 translocation.
PubMed:
Cytotoxic effects of new geranyl chalcone derivatives isolated from the leaves of Artocarpus communis in SW 872 human liposarcoma cells.
PubMed:
C-geranylated chalcones from the stems of Angelica keiskei with superoxide-scavenging activity.
PubMed:
Proteomic analysis of apoptosis induced by xanthoangelol, a major constituent of Angelica keiskei, in neuroblastoma.
PubMed:
Isobavachalcone, a chalcone constituent of Angelica keiskei, induces apoptosis in neuroblastoma.
PubMed:
Antidiabetic activities of chalcones isolated from a Japanese Herb, Angelica keiskei.
PubMed:
Beneficial effect of xanthoangelol, a chalcone compound from Angelica keiskei, on lipid metabolism in stroke-prone spontaneously hypertensive rats.
PubMed:
Geranylated phenolic constituents from the fruits of Artocarpus nobilis.
PubMed:
Chalcones and other compounds from the exudates of Angelica keiskei and their cancer chemopreventive effects.
PubMed:
Xanthoangelol, a major chalcone constituent of Angelica keiskei, induces apoptosis in neuroblastoma and leukemia cells.
PubMed:
Xanthoangelol D isolated from the roots of Angelica keiskei inhibits endothelin-1 production through the suppression of nuclear factor-kappaB.
PubMed:
Antitumor and antimetastatic activities of 4-hydroxyderricin isolated from Angelica keiskei roots.
PubMed:
Antitumor and antimetastatic activities of Angelica keiskei roots, part 1: Isolation of an active substance, xanthoangelol.
PubMed:
Artery relaxation by chalcones isolated from the roots of Angelica keiskei.
PubMed:
The effects of xanthoangelol E on arachidonic acid metabolism in the gastric antral mucosa and platelet of the rabbit.
PubMed:
Antibacterial activity of two chalcones, xanthoangelol and 4-hydroxyderricin, isolated from the root of Angelica keiskei KOIDZUMI.
PubMed:
Anti-tumor-promotion by principles obtained from Angelica keiskei.
PubMed:
Inhibition of gastric H+, K(+)-ATPase by chalcone derivatives, xanthoangelol and 4-hydroxyderricin, from Angelica keiskei Koidzumi.