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Sigma-Aldrich

Galangin

autophagy inducing flavonoid

Synonym(s):

3,5,7-Trihydroxyflavone, Norizalpinin

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About This Item

Empirical Formula (Hill Notation):
C15H10O5
CAS Number:
548-83-4
Molecular Weight:
270.24
Beilstein:
272179
EC Number:
208-960-4
MDL number:
MFCD00006833
UNSPSC Code:
41116107
PubChem Substance ID:
57648294
NACRES:
NA.79
Pricing and availability is not currently available.

Assay

≥95% (HPLC)

form

powder

color

yellow

mp

214-215 °C (lit.)

SMILES string

Oc1cc(O)c2C(=O)C(O)=C(Oc2c1)c3ccccc3

InChI

1S/C15H10O5/c16-9-6-10(17)12-11(7-9)20-15(14(19)13(12)18)8-4-2-1-3-5-8/h1-7,16-17,19H

InChI key

VCCRNZQBSJXYJD-UHFFFAOYSA-N

Gene Information

human ... ADORA2A(135) , ADORA3(140) , CYP1A2(1544)
rat ... Adora1(29290) , Adora2a(25369)

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General description

Galangin is a flavonoid isolated from members of the Zingiberaceae family, which are mainly used for herbal medicines.[1]

Application

Galangin has been used:
  • as a test drug to test its ameliorative effect in a rodent model of cisplatin-induced nephrotoxicity[1]
  • to test its effect on the differentiation of 3T3-L1 preadipocyte cells into adipocytes[2]
  • as an internal standard in nuclear magnetic resonance spectroscopy and mass spectroscopy[3]

Biochem/physiol Actions

Galangin exhibits antioxidant, anti-apoptotic, anti-inflammatory[1] and anti-obesity properties.[4] In addition, it also possesses anti-genotoxic activity against environmental and dietary carcinogens. Galangin inhibits cancer growth by hindering cancer cell proliferation, induction of apoptosis and autophagy and inhibition of metastasis.[5] Galangin also has an ability to inhibit CYP1A1 (Cytochrome P450, family 1, member A1) activity.[6]

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302

Precautionary Statements

P264 - P270 - P301 + P312 - P501

Hazard Classifications

Acute Tox. 4 Oral

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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Certificates of Analysis (COA)

Lot/Batch Number
MKCW1797
MKCR0752
MKCP6668
MKCL2067
MKCG0147

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Chemopreventive mechanisms of galangin against hepatocellular carcinoma: A review
Fang D, et al.
Biomedicine and Pharmacotherapy, 109(11), 2054-2061 (2019)
M Y Heo et al.
Mutation research, 488(2), 135-150 (2001-05-10)
Flavonoids are polyphenolic compounds that are present in plants. They have been shown to possess a variety of biological activities at non-toxic concentrations in organisms. Galangin, a member of the flavonol class of flavonoid, is present in high concentrations in
Ameesha Tomar et al.
Phytomedicine : international journal of phytotherapy and phytopharmacology, 34, 154-161 (2017-09-14)
Cisplatin is a widely used chemotherapeutic agent but now-a-days its usage is limited in clinical chemotherapy because of its severe nephrotoxic effect on renal tissues. Galangin, a flavonoid obtained from ginger family has been demonstrated to have antioxidant, anti-apoptotic and
Jung-Jin Lee et al.
Scientific reports, 7(1), 8207-8207 (2017-08-16)
In clinical pathology, stent interposition is used to treat vascular disease but can lead to restenosis. Drug-eluting stents (DES) are most commonly used to suppress restenosis but can also have side effects. Therefore, we investigated the anti-proliferative effect and its
The flavonoid galangin is an inhibitor of CYP1A1 activity and an agonist/antagonist of the aryl hydrocarbon receptor
Ciolino HP and Yeh GC
British Journal of Cancer, 79(9), 1340-1340 (1999)
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Dietary Antioxidants

Antioxidants protect biological systems from oxidative damage produced by oxygen-containing free radicals and from redoxactive transition metal ions such as iron, copper, and cadmium.

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