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Details

Stereochemistry ACHIRAL
Molecular Formula C15H10O5
Molecular Weight 270.2369
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of GALANGIN

SMILES

OC1=CC2=C(C(=O)C(O)=C(O2)C3=CC=CC=C3)C(O)=C1

InChI

InChIKey=VCCRNZQBSJXYJD-UHFFFAOYSA-N
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

HIDE SMILES / InChI

Molecular Formula C15H10O5
Molecular Weight 270.2369
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Galangin is a flavanol that is found in high concentrations in Alpinia officinarum and Helichrysum aureonitens. It can also be found in the rhizome of Alpinia galanga and in propolis. Galangin has been shown to have antibacterial, antiviral, anticancer and neuroprotective properties in vitro and in animal models.

CNS Activity

Curator's Comment: the referenced study was conducted on rat

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P11387|||Q9UJN0
Gene ID: 7150.0
Gene Symbol: TOP1
Target Organism: Homo sapiens (Human)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Studies on the interactions between some flavonols and cyclodextrins.
2007-11-01
Determination of flavonoid aglycones in several food samples by mixed micellar electrokinetic chromatography.
2007-10
Elastase release by stimulated neutrophils inhibited by flavonoids: importance of the catechol group.
2007-08-22
Mechanism and inhibitory effect of galangin and its flavonoid mixture from Alpinia officinarum on mushroom tyrosinase and B16 murine melanoma cells.
2007-08
Mechanism of inhibition of human secretory phospholipase A2 by flavonoids: rationale for lead design.
2007-08
Optimisation of an extraction procedure and chemical characterisation of Croatian propolis tinctures.
2007-07-13
Neutrophil effector functions triggered by Fc-gamma and/or complement receptors are dependent on B-ring hydroxylation pattern and physicochemical properties of flavonols.
2007-07-04
Esterase inhibition by grapefruit juice flavonoids leading to a new drug interaction.
2007-07
[Quantitative analysis of galangin from propolis in different areas by HPLC].
2007-05
Flavonoids possess neuroprotective effects on cultured pheochromocytoma PC12 cells: a comparison of different flavonoids in activating estrogenic effect and in preventing beta-amyloid-induced cell death.
2007-03-21
Inhibition of horseradish peroxidase catalytic activity by new 3-phenylcoumarin derivatives: synthesis and structure-activity relationships.
2007-02-01
Dietary flavonoids attenuate tumor necrosis factor alpha-induced adhesion molecule expression in human aortic endothelial cells. Structure-function relationships and activity after first pass metabolism.
2006-12-01
TCDD-induced CYP1A1 expression, an index of dioxin toxicity, is suppressed by flavonoids permeating the human intestinal Caco-2 cell monolayers.
2006-11-15
Influence of galangin on HL-60 cell proliferation and survival.
2006-11-08
Propolis from the northwest of Argentina as a source of antifungal principles.
2006-07
Flavonoids protect human retinal pigment epithelial cells from oxidative-stress-induced death.
2006-07
Antiparasitic activity of flavonoids and isoflavones against Cryptosporidium parvum and Encephalitozoon intestinalis.
2006-06
Combinatorial biosynthesis of flavones and flavonols in Escherichia coli.
2006-06
Methylation protects dietary flavonoids from rapid hepatic metabolism.
2006-05
In vitro antimicrobial activity of propolis samples from different geographical origins against certain oral pathogens.
2006-04-10
Inhibition of rat vas deferens contractions by flavonoids in-vitro.
2006-03
Dietary flavonoids: effects on xenobiotic and carcinogen metabolism.
2006-03
Chemical structure of flavonols in relation to modulation of angiogenesis and immune-endothelial cell adhesion.
2006-03
Assessment of the antibacterial activity of galangin against 4-quinolone resistant strains of Staphylococcus aureus.
2006-02
Vasorelaxant effect of the flavonoid galangin on isolated rat thoracic aorta.
2006-01-18
Inhibitors from the rhizomes of Alpinia officinarum on production of nitric oxide in lipopolysaccharide-activated macrophages and the structural requirements of diarylheptanoids for the activity.
2006-01-01
Use of the pig caecum model to mimic the human intestinal metabolism of hispidulin and related compounds.
2006-01
Growth of a human mammary tumor cell line is blocked by galangin, a naturally occurring bioflavonoid, and is accompanied by down-regulation of cyclins D3, E, and A.
2006
The effect of quercetin and galangin on glutathione reductase.
2005-12
Galangin protects pig detrusor nerves from repetitive field stimulation and anoxia/glucopenia injury.
2005-12
Human cytomegalovirus-inhibitory flavonoids: studies on antiviral activity and mechanism of action.
2005-12
Antiherpetic activities of flavonoids against herpes simplex virus type 1 (HSV-1) and type 2 (HSV-2) in vitro.
2005-11
Molecular targets of dietary polyphenols with anti-inflammatory properties.
2005-10-31
Detection of galangin-induced cytoplasmic membrane damage in Staphylococcus aureus by measuring potassium loss.
2005-10-03
The inhibitory effect of the flavonoid galangin on urinary bladder smooth muscle contractility is mediated in part by modulation of Ca2+ release from intracellular stores.
2005-10
Synthesis, spectral and electrochemical properties of Al(III) and Zn(II) complexes with flavonoids.
2005-07
Production of cytokine and NO by RAW 264.7 macrophages and PBMC in vitro incubation with flavonoids.
2005-05
Flavonoid galangin prevents smooth muscle fatigue of pig urinary bladder.
2005-05
The interaction of flavonoids with mitochondria: effects on energetic processes.
2005-04-15
[Xanthine oxidase inhibitory activity and hypouricemia effect of propolis in rats].
2005-03
Flavonoids and tyrosine nitration: structure-activity relationship correlation with enthalpy of formation.
2005-03
Quantitative structure activity relationship studies on the flavonoid mediated inhibition of multidrug resistance proteins 1 and 2.
2005-02-15
Multiple-signaling pathways are involved in the inhibitory effects of galangin on urinary bladder contractility.
2005
Chemical compositions and antimicrobial activities of four different Anatolian propolis samples.
2005
Galangin expresses bactericidal activity against multiple-resistant bacteria: MRSA, Enterococcus spp. and Pseudomonas aeruginosa.
2004-11-01
Inhibitory effect of flavonoids on N-acetylation of 5-aminosalicylic acid in cultured rat hepatocytes.
2004-09
Validated methods for the quantification of biologically active constituents of poplar-type propolis.
2004-08-18
Flavonoids induce apoptosis in human leukemia U937 cells through caspase- and caspase-calpain-dependent pathways.
2004
Antioxidant properties of complexes of flavonoids with metal ions.
2004
Antimicrobial constituents of Gomphrena martiana and Gomphrena boliviana.
1992-04
Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment: the referenced study was conducted on mice | the authors do not specify the route of administration
Specific-pathogen-free BALB/c mice aged 6-8 weeks were sensitized on days 0, 7 and 14 by intraperitoneal injection of 20 micro-g ovalbumin (OVA) emulsified in 2 mg of aluminum hydroxide gel in a total volume of 200 micro-L. Sensitised mice were exposed to aerosolized 5% OVA in sterile saline for 8 weeks beginning on day 16 for 30 min three times a week. Galangin at a dose of 0.1 or 0.5 mg/kg was administered 30 min before nebulized OVA.
Route of Administration: Unknown
Human MCF-7 cells were grown in RPMI-1640 media supplemented with 2 mM glutamine and 10% fetal bovine serum. Cells were sub-cultured weekly using 0.25% trypsin and 0.05% EDTA. All cultures were incubated at 37 deg-C under a 5% CO2 atmosphere. MCF-& cells in 175 cm^2 flasks were incubated in 12 mL of growth medium containing 0.1 micro-g/mL [3H]DMBA in the presence of DMSO, 1 micro-M galangin, or 10 micro-M galangin. After 24 hours, 1 mL of the medium was removed and extracted with 1 mL of ethyl acetate. [3H]DMBA was separated from metabolites and counted by scintilation.
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:34:02 GMT 2025
Edited
by admin
on Mon Mar 31 18:34:02 GMT 2025
Record UNII
142FWE6ECS
Record Status Validated (UNII)
Record Version
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Name Type Language
NSC-407229
Preferred Name English
GALANGIN
MI  
INCI  
Official Name English
4H-BENZOPYRAN-4-ONE, 3,5,7-TRIHYDROXY-2-PHENYL-
Systematic Name English
FLAVONE, 3,5,7-TRIHYDROXY-
Systematic Name English
NORIZALPININ
Common Name English
GALANGIN [MI]
Common Name English
3,5,7-TRIHYDROXYFLAVONE
Systematic Name English
3,5,7-TRIHYDROXY-2-PHENYL-4-BENZOPYRONE
Systematic Name English
Code System Code Type Description
CAS
548-83-4
Created by admin on Mon Mar 31 18:34:02 GMT 2025 , Edited by admin on Mon Mar 31 18:34:02 GMT 2025
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WIKIPEDIA
GALANGIN
Created by admin on Mon Mar 31 18:34:02 GMT 2025 , Edited by admin on Mon Mar 31 18:34:02 GMT 2025
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MERCK INDEX
m5639
Created by admin on Mon Mar 31 18:34:02 GMT 2025 , Edited by admin on Mon Mar 31 18:34:02 GMT 2025
PRIMARY Merck Index
ECHA (EC/EINECS)
208-960-4
Created by admin on Mon Mar 31 18:34:02 GMT 2025 , Edited by admin on Mon Mar 31 18:34:02 GMT 2025
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NSC
407229
Created by admin on Mon Mar 31 18:34:02 GMT 2025 , Edited by admin on Mon Mar 31 18:34:02 GMT 2025
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PUBCHEM
5281616
Created by admin on Mon Mar 31 18:34:02 GMT 2025 , Edited by admin on Mon Mar 31 18:34:02 GMT 2025
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EPA CompTox
DTXSID70203288
Created by admin on Mon Mar 31 18:34:02 GMT 2025 , Edited by admin on Mon Mar 31 18:34:02 GMT 2025
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FDA UNII
142FWE6ECS
Created by admin on Mon Mar 31 18:34:02 GMT 2025 , Edited by admin on Mon Mar 31 18:34:02 GMT 2025
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MESH
C037032
Created by admin on Mon Mar 31 18:34:02 GMT 2025 , Edited by admin on Mon Mar 31 18:34:02 GMT 2025
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CHEBI
5262
Created by admin on Mon Mar 31 18:34:02 GMT 2025 , Edited by admin on Mon Mar 31 18:34:02 GMT 2025
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