xanthoangelol
2',4,4'-trihydroxy-3'-geranylchalcone
 
Notes:
from angelica keiskei.
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      Product(s):
      62949-76-2 Xanthoangelol
       
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CAS Number: 62949-76-2Picture of molecule3D/inchi
FDA UNII: 91D4GN26Z1
Nikkaji Web: J20.204E
XlogP3-AA: 7.00 (est)
Molecular Weight: 392.49496000
Formula: C25 H28 O4
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
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)
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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:
BOC Sciences
For experimental / research use only.
Xanthoangelol
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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 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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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 : 643007
National Institute of Allergy and Infectious Diseases: Data
 (E)-1-[3-[(2E)-3,7-dimethylocta-2,6-dienyl]-2,4-dihydroxyphenyl]-3-(4-hydroxyphenyl)prop-2-en-1-one
Chemidplus: 0062949762
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References:
 (E)-1-[3-[(2E)-3,7-dimethylocta-2,6-dienyl]-2,4-dihydroxyphenyl]-3-(4-hydroxyphenyl)prop-2-en-1-one
NIST Chemistry WebBook: Search Inchi
Pubchem (cid): 643007
Pubchem (sid): 135081078
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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
CHEMBL: View
HMDB (The Human Metabolome Database): Search
FooDB: FDB001601
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
 ashitaba
Search Trop  Picture
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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
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Articles:
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.
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