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
Find a digital Reference Material for this product available on our online platform ChemisTwin® for NMR. You can use this digital equivalent on ChemisTwin® for your sample identity confirmation and compound quantification (with digital external standard). An NMR spectrum of this substance can be viewed and an online comparison against your sample can be performed with a few mouseclicks. Learn more here and start your free trial.
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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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
Whocely Victor de Castro et al.
Journal of agricultural and food chemistry, 56(12), 4840-4845 (2008-05-23)
The effect of two varieties of grapefruit juice (white and ruby red) and its selected components (naringin, naringenin, and bergamottin) was investigated on the activity of the P-glycoprotein (P-gp) in male Sprague-Dawley rats. Talinolol, a nonmetabolized P-gp substrate, was used
Narue Sakamaki et al.
Shokuhin eiseigaku zasshi. Journal of the Food Hygienic Society of Japan, 49(4), 326-331 (2008-09-13)
Interactions between grapefruit juice and medications have long been recognized. In recent years, several furanocoumarins (FCs) that inhibit P450 activity in intestinal microsomes have been isolated from grapefruit juice. FCs, i.e., bergamottin (BG), bergapten (BP), bergaptol (BT) and 6',7'-dihydroxybergamottin (DHB)
Marie Bräunlich et al.
Planta medica, 79(2), 137-141 (2012-12-20)
Extracts, subfractions, isolated anthocyanins and procyanidins, and two phenolic acids from aronia [Aronia melanocarpa] were investigated for their CYP3A4 inhibitory effects, using midazolam as the probe substrate and recombinant insect cell microsomes expressing CYP3A4 as the enzyme source. Procyanidin B5
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
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