01338
Bergamottin
analytical standard
Synonym(s):
Bergamotine, Bergaptin
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About This Item
Empirical Formula (Hill Notation):
C21H22O4
CAS Number:
Molecular Weight:
338.40
Beilstein:
1353914
MDL number:
UNSPSC Code:
85151701
PubChem Substance ID:
NACRES:
NA.24
Recommended Products
grade
analytical standard
Quality Level
Assay
≥98.0% (HPLC)
technique(s)
HPLC: suitable
gas chromatography (GC): suitable
mp
75-80 °C
application(s)
food and beverages
format
neat
storage temp.
2-8°C
SMILES string
C\C(C)=C\CC\C(C)=C\COc1c2C=CC(=O)Oc2cc3occc13
InChI
1S/C21H22O4/c1-14(2)5-4-6-15(3)9-11-24-21-16-7-8-20(22)25-19(16)13-18-17(21)10-12-23-18/h5,7-10,12-13H,4,6,11H2,1-3H3/b15-9+
InChI key
DBMJZOMNXBSRED-OQLLNIDSSA-N
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General description
Bergamottin, a member of the furanocoumarin family, is primarily found in grapefruit juice. It is reported to be a novel signal transducer and activator of the transcription 3 (STAT3) inhibitor. It is a known drug inhibitor of cytochrome P450 34A and also exhibits diverse anti-tumor and anti-inflammatory activities.
Application
Bergamottin may be used as an analytical standard to test its efficacy in the following:
- Blocker of STAT3 activation pathway in tumor cells; its potential in the therapy of multiple myeloma (MM) and other cancers is investigated.
- Prevention and the treatment of cancer via suppression of the NF-kB signaling pathway and its regulated gene products.
Packaging
Bottomless glass bottle. Contents are inside inserted fused cone.
Recommended products
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Storage Class Code
11 - Combustible Solids
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
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Hsia-Lien Lin et al.
Drug metabolism and disposition: the biological fate of chemicals, 40(5), 998-1006 (2012-02-22)
Previous studies have demonstrated that bergamottin (BG), a component of grapefruit juice, is a mechanism-based inactivator of CYP3A4 and contributes, in part, to the grapefruit juice-drug interaction. Although the covalent binding of [(14)C]BG to the CYP3A4 apoprotein has been demonstrated
Camelia Harapu Diaconu et al.
Revista medico-chirurgicala a Societatii de Medici si Naturalisti din Iasi, 115(1), 245-250 (2011-06-21)
Food-drug interactions are increasingly recognized as important clinical events which may change significantly the bioavailability of oral administrated drugs. Grapefruit juice (GFJ) demonstrated multiple interactions with drugs leading to loss of the therapeutic effects or increased side-effects. GFJ decreases pre-systemic
Jasminder Sahi et al.
Drug metabolism and disposition: the biological fate of chemicals, 30(2), 135-140 (2002-01-17)
Bergamottin, a furanocoumarin isolated from grapefruit juice, was investigated for the ability to increase diazepam bioavailability and for its effect on cytochrome P450 (P450) enzymes in the beagle dog liver and intestine. To study the effect of bergamottin on diazepam
Y Uesawa et al.
Die Pharmazie, 66(7), 525-528 (2011-08-05)
Grapefruit juice (GFJ) is known to affect the pharmacokinetics of a variety of drugs administered concomitantly and this is due to inhibition of intestinal CYP3A, a barrier protein for drug absorption. Some compounds such as furanocoumarin derivatives have been reported
Y Uesawa et al.
Die Pharmazie, 63(2), 110-112 (2008-04-03)
Bergamottin was identified as a cause of pharmacokinetic interaction with grapefruit juice intake and as a physiologically active substance involved in lipolysis. However, the quantification method on concentrations of bergamottin in systemic circulation has not been well established. The aim
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