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
UNSPSC Code:
85151701
NACRES:
NA.24
PubChem Substance ID:
MDL number:
Beilstein/REAXYS Number:
1353914
InChI key
DBMJZOMNXBSRED-OQLLNIDSSA-N
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+
grade
analytical standard
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
Quality Level
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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.
Other Notes
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
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
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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
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
Y Uesawa et al.
Die Pharmazie, 63(8), 598-600 (2008-09-06)
Colored (pink and red) grapefruit pulp contains lower amounts of the furanocoumarin derivatives that cause pharmacokinetic interactions than white grapefruit pulp. However, few studies have examined interactions with colored juice products. Therefore, we examined the potential interactions of both white
S Olguín-Reyes et al.
Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association, 50(9), 3094-3099 (2012-06-19)
Grapefruit juice (GJ) is a well known Cytochrome P450 (CYP) inhibitor; CYP3A is one of the most affected subfamily leading to anticarcinogenic and antimutagenic effects when GJ is administered to experimental animals in combination with mutagenic/carcinogenic agents metabolized by CYP3A.
Paul F Cancalon et al.
Journal of food science, 76(4), C543-C548 (2012-03-16)
Since the early 1990's, grapefruit juice has been implicated in drug interaction with various furanocoumarins (FCs) now associated with the effect. Although FCs are present in various fruits and vegetables, it is their presence in grapefruit that has attracted the
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