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01338

Supelco

Bergamottin

analytical standard

Synonyme(s) :

Bergamotine, Bergaptin

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About This Item

Formule empirique (notation de Hill):
C21H22O4
Numéro CAS:
7380-40-7
Poids moléculaire :
338.40
Numéro Beilstein :
1353914
Numéro MDL:
MFCD00017409
Code UNSPSC :
85151701
ID de substance PubChem :
329747253
Nomenclature NACRES :
NA.24

Qualité

analytical standard

Niveau de qualité

100

Pureté

≥98.0% (HPLC)

Technique(s)

HPLC: suitable
gas chromatography (GC): suitable

Pf

75-80 °C

Application(s)

food and beverages

Format

neat

Température de stockage

2-8°C

Chaîne SMILES 

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+

Clé InChI

DBMJZOMNXBSRED-OQLLNIDSSA-N

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Catégories apparentées

Description générale

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.

Conditionnement

Bottomless glass bottle. Contents are inside inserted fused cone.

Produits recommandés

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.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)

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Certificats d'analyse (COA)

Lot/Batch Number
BCCL0244
BCCJ7166
BCCJ0282
BCCD6554
BCBV9499

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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)
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
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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