EU/US Properties Organoleptics Cosmetics Suppliers Safety Safety in use Safety references References Other Blenders Uses Occurrence Synonyms Articles Notes
 

bavachinin
4'-hydroxy-7-methoxy-6-prenylflavanone

Supplier Sponsors

Name:2-(4-hydroxyphenyl)-7-methoxy-6-(3-methylbut-2-enyl)-2,3-dihydrochromen-4-one
CAS Number: 19879-30-2Picture of molecule3D/inchi
FDA UNII: VL3EV483SZ
Beilstein Number:3629340
MDL:MFCD06858307
XlogP3-AA:4.40 (est)
Molecular Weight:338.40314000
Formula:C21 H22 O4
NMR Predictor:Predict (works with chrome, Edge or firefox)
Category:natural substances and extractives
 
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Google Scholar:Search
Google Books:Search
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Google Scholar: with word "odor"Search
Google Patents:Search
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: 537.12 °C. @ 760.00 mm Hg (est)
Flash Point: 375.00 °F. TCC ( 190.30 °C. ) (est)
logP (o/w): 3.946 (est)
Soluble in:
 water, 0.945 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.
Bavachinin A 98%
BOC Sciences
For experimental / research use only.
Bavachinin >98%
Carbosynth
For experimental / research use only.
Bavachinin
Coompo
For experimental / research use only.
Bavachinin from Plants ≥96%
Odor: characteristic
Use: Hypoxia-inducible factor-1 (HIF-1) consists of two subunits, the HIF-1β, which is constitutively expressed, and HIF-1a, which is oxygen-responsive. HIF-1a is over-expressed in response to hypoxia, increasing transcriptional activity linked to tumor progression, angiogenesis, metastasis, and invasion. Bavachinin inhibited increases in HIF-1a activity in human KB carcinoma (HeLa cell derivative) and human HOS osteosarcoma cells under hypoxia in a concentration-dependent manner, probably by enhancing the interaction between von Hippel-Lindau (VHL) and HIF-1a. Furthermore, Bavachinin decreased transcription of genes associated with angiogenesis and energy metabolism that are regulated by HIF-1, such as vascular endothelial growth factors (VEGF), Glut 1 and Hexokinase 2. Bavachinin also inhibited tube formation in human umbilical vein endothelial cells (HUVECs) as well as in vitro migration of KB cells. In vivo studies showed that injecting Bavachinin thrice weekly for four weeks significantly reduced tumor volume and CD31 expression in nude mice with KB xenografts. These data indicate that Bavachinin could be used as a therapeutic agent for inhibiting tumor angiogenesis.
ExtraSynthese
For experimental / research use only.
Bavachinin (HPLC) ≥99%
Sigma-Aldrich: Sigma
For experimental / research use only.
Bavachinin
sds
 
Safety Information:
Preferred SDS: View
 
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:
oral-mouse LD > 1000 mg/kg
Indian Drugs. Vol. 29, Pg. 662, 1992.

Dermal Toxicity:
Not determined
Inhalation Toxicity:
Not determined
 
Safety in Use Information:
Category:
natural substances and extractives
Recommendation for bavachinin usage levels up to:
 not for fragrance use.
 
Recommendation for bavachinin 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 :122835
National Institute of Allergy and Infectious Diseases:Data
WGK Germany:3
2-(4-hydroxyphenyl)-7-methoxy-6-(3-methylbut-2-enyl)-2,3-dihydrochromen-4-one
Chemidplus:0019879302
 
References:
 2-(4-hydroxyphenyl)-7-methoxy-6-(3-methylbut-2-enyl)-2,3-dihydrochromen-4-one
NIST Chemistry WebBook:Search Inchi
Pubchem (cid):122835
Pubchem (sid):135080093
 
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
HMDB (The Human Metabolome Database):Search
VCF-Online:VCF Volatile Compounds in Food
ChemSpider:View
Wikipedia:View
 
Potential Blenders and core components note
None Found
 
Potential Uses:
None Found
 
Occurrence (nature, food, other):note
 psoralea corilifolia seed
Search Trop Picture
 
Synonyms:
 bavachinin A
4H-1-benzopyran-4-one, 2,3-dihydro-2-(4-hydroxyphenyl)-7-methoxy-6-(3-methyl-2-buten-1-yl)-
 flavanone, 4'-hydroxy-7-methoxy-6-(3-methyl-2-butenyl)- (8CI)
4'-hydroxy-7-methoxy-6-(3-methyl-2-butenyl) flavanone
4'-hydroxy-7-methoxy-6-(3-methyl-2-butenyl)flavanone
4'-hydroxy-7-methoxy-6-prenylflavanone
2-(4-hydroxyphenyl)-7-methoxy-6-(3-methyl-2-buten-1-yl)-2,3-dihydro-4H-chromen-4-one
2-(4-hydroxyphenyl)-7-methoxy-6-(3-methylbut-2-en-1-yl)-2,3-dihydro-4H-chromen-4-one
2-(4-hydroxyphenyl)-7-methoxy-6-(3-methylbut-2-enyl)-2,3-dihydro-4H-chromen-4-one
2-(4-hydroxyphenyl)-7-methoxy-6-(3-methylbut-2-enyl)-2,3-dihydrochromen-4-one
7-ortho-methyl bavachin
 

Articles:

PubMed:Estrogenic activities of Psoralea corylifolia L. seed extracts and main constituents.
PubMed:Isolation of antioxidants from Psoralea corylifolia fruits using high-speed counter-current chromatography guided by thin layer chromatography-antioxidant autographic assay.
PubMed:[Constituent of natural food additive hokosshi extract and an analytical method for the additive in foods].
PubMed:Antioxidative components of Psoralea corylifolia (Leguminosae).
PubMed:Antiinflamatory, antipyretic & analgesic properties of bavachinin-a flavanone isolated from seeds of Psoralea corylifolia Linn. (Babchi).
PubMed:Screening of neuraminidase inhibitors from traditional Chinese medicines by integrating capillary electrophoresis with immobilized enzyme microreactor.
PubMed:Effect of Bavachinin and its derivatives on T cell differentiation.
PubMed:[Chemical constituents from Psoralea corylifolia and their antioxidant alpha-glucosidase inhibitory and antimicrobial activities].
PubMed:Treatment of allergic inflammation and hyperresponsiveness by a simple compound, Bavachinin, isolated from Chinese herbs.
PubMed:Biotransformation of bavachinin by three fungal cell cultures.
PubMed:Isobavachalcone and bavachinin from Psoraleae Fructus modulate Aβ42 aggregation process through different mechanisms in vitro.
PubMed:Psoralea corylifolia L. (Buguchi) - folklore to modern evidence: review.
PubMed:Phenolic phytochemical displaying SARS-CoV papain-like protease inhibition from the seeds of Psoralea corylifolia.
PubMed:Studies on lymphangiogenesis inhibitors from Korean and Japanese crude drugs.
PubMed:Anti-angiogenic and anti-tumor activity of Bavachinin by targeting hypoxia-inducible factor-1α.
PubMed:Phenolic compounds isolated from Psoralea corylifolia inhibit IL-6-induced STAT3 activation.
PubMed:Development of a fully automated on-line solid phase extraction and high-performance liquid chromatography with diode array detection method for the pharmacokinetic evaluation of bavachinin: a study on absolute bioavailability and dose proportionality.
PubMed:Isolation of antioxidants from Psoralea corylifolia fruits using high-speed counter-current chromatography guided by thin layer chromatography-antioxidant autographic assay.
PubMed:Bioactive constituents from Chinese natural medicines. XXXIII. Inhibitors from the seeds of Psoralea corylifolia on production of nitric oxide in lipopolysaccharide-activated macrophages.
PubMed:In vitro BACE-1 inhibitory phenolic components from the seeds of Psoralea corylifolia.
PubMed:Chemical fingerprint and quantitative analysis of fructus psoraleae by high-performance liquid chromatography.
PubMed:Antioxidative components of Psoralea corylifolia (Leguminosae).
PubMed:Comparative analysis of the effects of flavonoids on proliferation, cytotoxicity, and apoptosis in human colon cancer cell lines.
 
Notes:
None found
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