All Photos(1)
Synonym(s):
Bergamotine, Bergaptin
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
Looking for similar products? Visit Product Comparison Guide
Related Categories
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.
WGK
WGK 3
Flash Point(F)
Not applicable
Flash Point(C)
Not applicable
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Gloves
Certificates of Analysis (COA)
Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.
Already Own This Product?
Find documentation for the products that you have recently purchased in the Document Library.
Anastasia Messer et al.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association, 49(12), 3224-3231 (2011-09-29)
Furocoumarins are phototoxic and photogenotoxic natural plant constituents occurring in cosmetics, food and drugs. Grapefruit juice is considered as a major dietary source of furocoumarins although few is known about the variability of furocoumarins in grapefruit juice. We analyzed the
Yong Pil Hwang et al.
Molecular nutrition & food research, 54(7), 977-990 (2009-11-28)
Matrix metalloproteinase (MMP) plays an important role in the invasion and metastasis of cancer cells. The inhibitory effects of bergamottin, a cytochrome P450 inhibitor from Citrus paradis (grapefruit), on tumor invasion and migration and the possible mechanisms involved in this
Simvastatin in combination with bergamottin potentiates TNF-induced apoptosis through modulation of NF-?B signalling pathway in human chronic myelogenous leukaemia
Kim M-S, et al.
Pharmaceutical biology, 54(10), 2050-2060 (2016)
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
Kyung Myung et al.
Applied microbiology and biotechnology, 78(2), 343-349 (2008-01-10)
Fungi metabolize polycyclic aromatic hydrocarbons by a number of detoxification processes, including the formation of sulfated and glycosidated conjugates. A class of aromatic compounds in grapefruit is the furanocoumarins (FCs), and their metabolism in humans is centrally involved in the
Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.
Contact Technical Service