Galangin

Galangin

IUPAC name 3,5,7-trihydroxy-2-phenylchromen-4-one
Other names Norizalpinin 3,5,7-Trihydroxyflavone 3,5,7-triOH-Flavone
Identifiers
CAS number	548-83-4^Y
PubChem	5281616
ChemSpider	4444935^Y
UNII	142FWE6ECS^Y
KEGG	C10044^Y
ChEBI	CHEBI:5262^Y
ChEMBL	CHEMBL309490^Y
IUPHAR ligand	410
Jmol-3D images	Image 1
SMILES O=C1c3c(O/C(=C1/O)c2ccccc2)cc(O)cc3O
InChI 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^Y Key: VCCRNZQBSJXYJD-UHFFFAOYSA-N^Y InChI=1/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 Key: VCCRNZQBSJXYJD-UHFFFAOYAC
Properties
Molecular formula	C₁₅H₁₀O₅
Molar mass	270.24 g/mol
Exact mass	270.052823 u
Melting point	214–215 °C
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Galangin is a flavonol found in high concentrations in Alpinia officinarum (lesser galangal).^[1] It is also found in the galangal rhizome (Alpinia galanga)^[2] and in propolis.^[3] Galangin has been shown to slow the increase and growth of breast tumor cells in vitro.^[4]^[5]

References

^ Ciolino, H. P.; Yeh, G. C. (1999). "The flavonoid galangin is an inhibitor of CYP1A1 activity and an agonist/antagonist of the aryl hydrocarbon receptor". British Journal of Cancer 79 (9/10): 1340–1346. doi:10.1038/sj.bjc.6690216. edit
^ Kaur, A.; Singh, R.; Dey, C. S.; Sharma, S. S.; Bhutani, K. K.; Singh, I. P. (2010). "Antileishmanial phenylpropanoids from Alpinia galanga (Linn.) Willd". Indian Journal of Experimental Biology 48 (3): 314–317. PMID 21046987. http://nopr.niscair.res.in/bitstream/123456789/7407/1/IJEB%2048(3)%20314-317.pdf. edit
^ Tosi, E; Re, E; Ortega, M; Cazzoli, A (2007). "Food preservative based on propolis: Bacteriostatic activity of propolis polyphenols and flavonoids upon Escherichia coli". Food Chemistry 104: 1025. doi:10.1016/j.foodchem.2007.01.011. edit
^ So, F. V.; Guthrie, N.; Chambers, A. F.; Moussa, M.; Carroll, K. K. (1996). "Inhibition of human breast cancer cell proliferation and delay of mammary tumorigenesis by flavonoids and citrus juices". Nutrition and Cancer 26 (2): 167–181. doi:10.1080/01635589609514473. PMID 8875554. edit
^ So, F.; Guthrie, N.; Chambers, A. F.; Carroll, K. K. (1997). "Inhibition of proliferation of estrogen receptor-positive MCF-7 human breast cancer cells by flavonoids in the presence and absence of excess estrogen". Cancer Letters 112 (2): 127–133. doi:10.1016/S0304-3835(96)04557-0. PMID 9066718. edit

Flavonols and their conjugates

Backbone

Aglycones	3-Hydroxyflavone (synthetic) and derivatives

Aglycones

Conjugates

Glycosides of herbacetin

Rhodionin | Rhodiosin

Glycosides of kaempferol

Glycosides of myricetin

Myricetin 3-O-rutinoside | Myricetin-3-O-neohesperidoside | Myricitrin

Conjugates of quercetin

Sulfates	Quercetin 3-O-sulfate \| Quercetin 3,3'-bissulfate \| Quercetin 3,4'-bissulfate

Glycosides	CTN-986 \| Guaijaverin (quercetin 3-O-arabinoside) \| Heliosin (Quercetin 3-digalactoside) \| Hyperoside \| Isoquercitin \| Miquelianin \| Quercetin-3-sophorodide \| Quercitrin \| Rutin \| Spiraeoside

O-Methylated flavonols

Aglycones	5-O-methylmyricetin \| Annulatin \| Ayanin \| Axillarin \| Azaleatin \| Brickellin \| Centaureidin \| Chrysosplenetin \| Combretol \| Ermanin \| Eupatolitin \| Eupalitin \| Europetin \| Isorhamnetin \| Jaceidin \| Kaempferide \| Kumatakenin \| Laricitrin \| Natsudaidain \| Ombuin \| Pachypodol \| Patuletin \| Retusin \| Mearnsetin \| Rhamnazin \| Rhamnetin \| Santin \| Spinacetin \| Syringetin \| Tamarixetin

Glycosides	Azalein \| Centaurein \| Eupalin \| Eupatolin \| Jacein \| Patulitrin \| Tamarixetin 7-rutinoside \| Xanthorhamnin

Derivative flavonols

Aglycones	Noricaritin \| Dihydronoricaritin

Glycosides	Amurensin \| Icariin \| Phelloside \| Dihydrophelloside \| Rutin S

Pyranoflavonols

Aglycones	Karanjachromene

Furanoflavonols

Semisynthetic

Glycosides	Hydroxyethylrutosides (Monoxerutin, Troxerutin)