Pinocembrin

Pinocembrin
Names
	IUPAC name 5,7-Dihydroxy-2-phenyl-2,3-dihydro-4H-chromen-4-one
	Other names Dihydrochrysin; Galangin flavanone; 5,7-Dihydroxyflavanone; 5,7-Dihydroxy-2-phenyl-2,3-dihydro-4H-chromen-4-one; 4H-1-Benzopyran-4-one, 2,3-dihydro-5,7-dihydroxy-2-phenyl-; 5,7-Dihydroxy-2-phenyl-chroman-4-one
Identifiers
CAS Number	68745-38-0 (±) ; 480-39-7 (S)-(+); 206660-42-6 (R)-(-);
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:28157 ;
ChEMBL	ChEMBL399910 ;
ChemSpider	208593 ;
PubChem CID	238782;
CompTox Dashboard (EPA)	DTXSID80285959 DTXSID3075412, DTXSID80285959 ;
	InChI InChI=1S/C15H12O4/c16-10-6-11(17)15-12(18)8-13(19-14(15)7-10)9-4-2-1-3-5-9/h1-7,13,16-17H,8H2 Key: URFCJEUYXNAHFI-UHFFFAOYSA-N ; InChI=1/C15H12O4/c16-10-6-11(17)15-12(18)8-13(19-14(15)7-10)9-4-2-1-3-5-9/h1-7,13,16-17H,8H2 Key: URFCJEUYXNAHFI-UHFFFAOYAA;
	SMILES O=C2c3c(OC(c1ccccc1)C2)cc(O)cc3O;
Properties
Chemical formula	C15H12O4
Molar mass	256.257 g·mol−1
Density	1.386 g/mL
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Pinocembrin is a flavanone, a type of flavonoid. It is an antioxidant found in damiana,^[1] honey, fingerroot,^[2] and propolis.^[3]

Pinocembrin can be converted biosynthetically to pinobanksin by hydroxylation adjacent to the ketone. Studies have shown that pinocembrin has potential as a drug to treat cerebral ischemia, intracerebral hemorrhage, neurodegenerative diseases, cardiovascular diseases and atherosclerosis as well as other diseases.^[4]^[5]

References

^ Zhao, J; Dasmahapatra AK; Khan SI; Khan IA (Dec 2008). "Anti-aromatase activity of the constituents from damiana (Turnera diffusa)". J Ethnopharmacol. 120 (3): 387–393. doi:10.1016/j.jep.2008.09.016. PMID 18948180.
^ Punvittayagul, C; Wongpoomchai R; Taya S; Pompimon W. (January 2011). "Effect of pinocembrin isolated from Boesenbergia pandurata on xenobiotic-metabolizing enzymes in rat liver". Drug Metabolism Letters. 5 (1): 1–5. doi:10.2174/187231211794455226. PMID 20942797.
^ Bosio K; Avanzini C; D’Avolio A; Ozino O; Savoia D (2000). "In vitro activity of propolis against Streptococcus pyogenes". Letters in Applied Microbiology. 31 (2): 174–177. doi:10.1046/j.1365-2672.2000.00785.x. PMID 10972723.
^ Lan X, Wang W, Li Q, Wang J (April 2016). "The natural flavonoid pinocembrin: molecular targets and potential therapeutic applications". Mol Neurobiol. 53 (3): 1794–801. doi:10.1007/s12035-015-9125-2. PMC 4561606. PMID 25744566.
^ Lan X, Han X, Li Q, Li Q, Gao Y, Cheng T, Wan J, Zhu W, Wang J, Lan X, Wang W, Li Q, Wang J (March 2017). "Pinocembrin protects hemorrhagic brain primarily by inhibiting toll-like receptor 4 and reducing M1 phenotype microglia". Brain Behav. Immun. 61: 326–339. doi:10.1016/j.bbi.2016.12.012. PMC 5453178. PMID 28007523.

External links

Media related to Pinocembrin at Wikimedia Commons

[1] Zhao, J; Dasmahapatra AK; Khan SI; Khan IA (Dec 2008). "Anti-aromatase activity of the constituents from damiana (Turnera diffusa)". J Ethnopharmacol. 120 (3): 387–393. doi:10.1016/j.jep.2008.09.016. PMID 18948180.

[2] Punvittayagul, C; Wongpoomchai R; Taya S; Pompimon W. (January 2011). "Effect of pinocembrin isolated from Boesenbergia pandurata on xenobiotic-metabolizing enzymes in rat liver". Drug Metabolism Letters. 5 (1): 1–5. doi:10.2174/187231211794455226. PMID 20942797.

[pmid10972723-3] Bosio K; Avanzini C; D’Avolio A; Ozino O; Savoia D (2000). "In vitro activity of propolis against Streptococcus pyogenes". Letters in Applied Microbiology. 31 (2): 174–177. doi:10.1046/j.1365-2672.2000.00785.x. PMID 10972723.

[pmid25744566-4] Lan X, Wang W, Li Q, Wang J (April 2016). "The natural flavonoid pinocembrin: molecular targets and potential therapeutic applications". Mol Neurobiol. 53 (3): 1794–801. doi:10.1007/s12035-015-9125-2. PMC 4561606. PMID 25744566.

[pmid_28007523-5] Lan X, Han X, Li Q, Li Q, Gao Y, Cheng T, Wan J, Zhu W, Wang J, Lan X, Wang W, Li Q, Wang J (March 2017). "Pinocembrin protects hemorrhagic brain primarily by inhibiting toll-like receptor 4 and reducing M1 phenotype microglia". Brain Behav. Immun. 61: 326–339. doi:10.1016/j.bbi.2016.12.012. PMC 5453178. PMID 28007523.

[1]

[2]

[3]

[4]

[5]

Names

IUPAC name 5,7-Dihydroxy-2-phenyl-2,3-dihydro-4H-chromen-4-one
Other names Dihydrochrysin Galangin flavanone 5,7-Dihydroxyflavanone 5,7-Dihydroxy-2-phenyl-2,3-dihydro-4H-chromen-4-one 4H-1-Benzopyran-4-one, 2,3-dihydro-5,7-dihydroxy-2-phenyl- 5,7-Dihydroxy-2-phenyl-chroman-4-one
Identifiers
CAS Number	68745-38-0 (±) 480-39-7 (S)-(+) 206660-42-6 (R)-(-)
3D model (JSmol)	Interactive image
ChEBI	CHEBI:28157
ChEMBL	ChEMBL399910
ChemSpider	208593
PubChem CID	238782
CompTox Dashboard (EPA)	DTXSID80285959 DTXSID3075412, DTXSID80285959
InChI InChI=1S/C15H12O4/c16-10-6-11(17)15-12(18)8-13(19-14(15)7-10)9-4-2-1-3-5-9/h1-7,13,16-17H,8H2 Key: URFCJEUYXNAHFI-UHFFFAOYSA-N InChI=1/C15H12O4/c16-10-6-11(17)15-12(18)8-13(19-14(15)7-10)9-4-2-1-3-5-9/h1-7,13,16-17H,8H2 Key: URFCJEUYXNAHFI-UHFFFAOYAA
SMILES O=C2c3c(OC(c1ccccc1)C2)cc(O)cc3O
Properties
Chemical formula	C₁₅H₁₂O₄
Molar mass	256.257 g·mol⁻¹
Density	1.386 g/mL
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Pinocembrin

See also

References

External links