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artemetin
combretol

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Name:2-(3,4-dimethoxyphenyl)-5-hydroxy-3,6,7-trimethoxychromen-4-one
CAS Number: 479-90-3Picture of molecule3D/inchi
FDA UNII: 73KMT7R64H
Nikkaji Web:J12.181I
XlogP3-AA:3.40 (est)
Molecular Weight:388.37300000
Formula:C20 H20 O8
BioActivity Summary:listing
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
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US Patents:Search
EU Patents:Search
Pubchem Patents:Search
PubMed:Search
NCBI:Search
 
Physical Properties:
Assay: 95.00 to 100.00
Food Chemicals Codex Listed: No
Boiling Point: 588.80 °C. @ 760.00 mm Hg (est)
Flash Point: 408.00 °F. TCC ( 208.90 °C. ) (est)
logP (o/w): 2.550 (est)
Soluble in:
 water, 54.85 mg/L @ 25 °C (est)
 
Organoleptic Properties:
Odor and/or flavor descriptions from others (if found).
 
Cosmetic Information:
None found
 
Suppliers:
Alfa Biotechnology
For experimental / research use only.
Artemitin 98%
BOC Sciences
For experimental / research use only.
Artemetin 99%
Odor: characteristic
Use: Artemetin comes from the herbs of Achillea millefolium L. Acting as antioxidant and antiapoptotic agent and through the activation of ERK1/2 and Akt, Artemetin protects endothelial function. antiproliferative; inhibits apoptosis; anti-inflammatory
Coompo
For experimental / research use only.
Artemetin from Plants ≥96%
Odor: characteristic
Use: The artemetin showed marked anti-inflammatory activity using various experimental models in rats. Artemetin significantly inhibited carrageenin-induced paw edema following oral doses from 30.4 to 153.9 mg.kg-1. The doses of 102.6 and 153.9 mg.kg-1 showed an inhibitory effect similar to that of 50.0 mg.kg-1 of calcium phenylbutazone. The ED50 value of artemetin in rats was estimated to be 67.07 mg.kg-1. Repeated administration of artemetin at doses of 67.07 mg.kg-1 for a 6-day period reduced granuloma formation with a response comparable to that of 20.0 mg.kg-1 of calcium phenylbutazone. This same dose of artemetin also reduced the vascular permeability to intracutaneous histamine. Sub-acute toxicological experiments indicated a very low toxicity. This flavonoid was able to dose-dependently reduce the MAP, up to 11.47 ± 1.5 mm Hg (1.5 mg/kg, i.v.). To investigate if artemetin-induced hypotension was related to angiotensin-converting enzyme inhibition, we evaluated the influence of this flavonoid on the vascular effects of both angiotensin I and bradykinin. Intravenous injection of artemetin (0.75 mg/kg) significantly reduced the hypertensive response to angiotensin I while increased the average length of bradykinin-induced hypotension. Artemetin (1.5 mg/kg, p.o.) was also able to reduce plasma (about 37%) and vascular (up to 63%) ACE activity in vitro, compared to control group. On the other hand, artemetin did not change angiotensin II-induced hypertension. Our study disclosed that this effect may be, at least in part, associated with high levels of artemetin and its ability to decrease angiotensin II generation in vivo, by ACE inhibition.
 
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
 
Safety in Use Information:
Category:
natural substances and extractives
Recommendation for artemetin usage levels up to:
 not for fragrance use.
 
Recommendation for artemetin flavor usage levels up to:
 not for flavor use.
 
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 :5320351
National Institute of Allergy and Infectious Diseases:Data
2-(3,4-dimethoxyphenyl)-5-hydroxy-3,6,7-trimethoxychromen-4-one
Chemidplus:0000479903
 
References:
 2-(3,4-dimethoxyphenyl)-5-hydroxy-3,6,7-trimethoxychromen-4-one
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):5320351
Pubchem (sid):135026029
 
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):HMDB30095
FooDB:FDB001546
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
Wikipedia2:View2
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 verbena
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Synonyms:
 artemisetin
4H-1-benzopyran-4-one, 2-(3,4-dimethoxyphenyl)-5-hydroxy-3,6,7-trimethoxy-
 combretol
2-(3,4-dimethoxyphenyl)-5-hydroxy-3,6,7-trimethoxy-4H-1-benzopyran-4-one
2-(3,4-dimethoxyphenyl)-5-hydroxy-3,6,7-trimethoxy-4H-chromen-4-one
2-(3,4-dimethoxyphenyl)-5-hydroxy-3,6,7-trimethoxychromen-4-one
 erianthin
 flavone, 5-hydroxy-3,3',4',6,7-pentamethoxy-
5-hydroxy-3,3',4',6,7-pentamethoxyflavone
5-hydroxy-3,6,7,3',4'-pentamethoxyflavone
 penta-O-methylquercetagetin
 quercetagetin-3,6,7,3',4'-pentamethylether
 

Articles:

PubMed:In vitro Antitumoral Activity of Compounds Isolated from Artemisia gorgonum Webb.
PubMed:Antiproliferative effect of flavonoids from the halophyte Vitex rotundifolia on human cancer cells.
PubMed:The effect of O-methylated flavonoids and other co-metabolites on the crystallization and purification of artemisinin.
PubMed:[Chemical constituents from ethyl acetate extract of Artemisia rupestris].
PubMed:Compounds from the Fruits of the Popular European Medicinal Plant Vitex agnus-castus in Chemoprevention via NADP(H):Quinone Oxidoreductase Type 1 Induction.
PubMed:The flavonoids casticin and artemetin are poorly extracted and are unstable in an Artemisia annua tea infusion.
PubMed:Bioactive diterpenes from Callicarpa longissima.
PubMed:Antioxidant and hepatoprotective effects of ethanol extract of Vitex glabrata on carbon tetrachloride-induced liver damage in rats.
PubMed:Furfuran lignans and a flavone from Artemisia gorgonum Webb and their in vitro activity against Plasmodium falciparum.
PubMed:Hypotensive mechanism of the extracts and artemetin isolated from Achillea millefolium L. (Asteraceae) in rats.
PubMed:[Preparative isolation and purification of the active components from Viticis Fructus by high-speed counter-current chromatography].
PubMed:One new triterpene ester from Nepeta suavis.
PubMed:Chemical composition and antibacterial activity of Cordia verbenacea extracts obtained by different methods.
PubMed:A high-speed counter-current chromatography- HPLC-DAD method for preparative isolation and purification of two polymethoxylated flavones from Taraxacum mongolicum.
PubMed:Antiinflammatory and lipoxygenase inhibitory compounds from Vitex agnus-castus.
PubMed:Antiproliferative effect of flavonoids and sesquiterpenoids from Achillea millefolium s.l. on cultured human tumour cell lines.
PubMed:[Studies on chemical constituents from herbs of Taraxacum mongolicum].
PubMed:[Studies on constitutes from Taraxacum mongolicum].
PubMed:[Studies on chemical constituents in herb from Artemisia rupestris].
PubMed:Flavonoids from Vitex trifolia L. inhibit cell cycle progression at G2/M phase and induce apoptosis in mammalian cancer cells.
PubMed:Phenolic compounds and flavonoids as plant growth regulators from fruit and leaf of Vitex rotundifolia.
PubMed:G2-M arrest and antimitotic activity mediated by casticin, a flavonoid isolated from Viticis Fructus (Vitex rotundifolia Linne fil.).
PubMed:Evaluation of the antiedematogenic activity of artemetin isolated from Cordia curassavica DC.
PubMed:New diterpenes and norditerpenes from the fruits of Vitex rotundifolia.
PubMed:In vitro cytotoxicity of flavonoids against MK2 and C6 tumour cells.
PubMed:Polymethoxyflavonoids from Vitex rotundifolia inhibit proliferation by inducing apoptosis in human myeloid leukemia cells.
PubMed:Terpenoids and flavonoids from Artemisia species.
PubMed:Evaluation of the total peroxyl radical-scavenging capacity of flavonoids: structure-activity relationships.
PubMed:Cytotoxic flavonoids from Vitex agnus-castus.
PubMed:Cytotoxic terpenoids and flavonoids from Artemisia annua.
PubMed:Antimalarial activity of Artemisia annua flavonoids from whole plants and cell cultures.
PubMed:Anti-inflammatory activity and sub-acute toxicity of artemetin.
PubMed:Chemical Constituents of Buxus sempervirens.
PubMed:Potentiation of the antimalarial activity of qinghaosu by methoxylated flavones.
PubMed:Isolation and identification of three new flavones from Achillea millefolium L.
 
Notes:
Constit. of Artemisia spp., Kuhnia eupatorioides (preferred genus name Brickellia), Achillea spp., Brickellia spp. and others in the Compositae [CCD]
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