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(+)-Pinocembrin

HCID 68071
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Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
480-39-7
Standard SMILES
O=C1C[C@@H](c2ccccc2)Oc2cc(O)cc(O)c21
InChIKey
URFCJEUYXNAHFI-ZDUSSCGKSA-N
Molecular formula
C15H12O4
Average molar mass
256.25 g/mol
Monoisotopic mass
256.07355886

Overview

Pinocembrin is a dihydroxyflavanone in which the two hydroxy groups are located at positions 5 and 7. A natural product found in Piper sarmentosum and Cryptocarya chartacea. It has a role as an antioxidant, a metabolite, an antineoplastic agent, a vasodilator agent and a neuroprotective agent. It is a (2S)-flavan-4-one and a dihydroxyflavanone.

Names & identifiers

Preferred name
(+)-Pinocembrin
IUPAC
(2S)-5,7-dihydroxy-2-phenyl-2,3-dihydrochromen-4-one
English name
PINOCEMBRIN
Molecular formula
C15H12O4
Molecular weight
256.25

Names & synonyms

Pinocembrin480-39-7(+)-PinocembrinGalangin flavanonepinocembrine(+)-pinocoembrin(S)-2,3-Dihydro-5,7-dihydroxy-2-phenyl-4H-1-benzopyran-4-one4H-1-Benzopyran-4-one, 2,3-dihydro-5,7-dihydroxy-2-phenyl-, (2S)-8T7C8CH791(2S)-5,7-dihydroxy-2-phenyl-2,3-dihydrochromen-4-one5,7-dihydroxy-flavanoneNSC-279005
Show more names
5,7-DIHYDROXYFLAVANONEPicembrinpinocemberinPinocembrin-RMPINOCEMBRIN(RG)galanginflavanonePinocembrin (Standard)
DTXSID3075412CHEBI:28157RefChem:863359DTXCID0040597Dihydrochrysin(S)-5,7-dihydroxy-2-phenylchroman-4-one(2S)-pinocembrin(S)-5,7-dihydroxyflavanone

Database identifiers

CAS
480-39-7
PubChem CID
68071

Properties

Computed structural properties

XLogP
2.7
Topological polar surface area
66.8 Ų
Hydrogen bond donors
2
Hydrogen bond acceptors
4
Rotatable bonds
1
Heavy atoms
19
Formal charge
0
Complexity
337

Experimental & physicochemical properties

LipidsPolyketides [PK] -> Flavonoids [PK12] -> Flavanones [PK1214]
Endocrine DisruptorsPotential endocrine disrupting compound
Melting Point192 - 193 °C
Physical DescriptionSolid

Physicochemical properties

Melting point
202 °C · 202 °C
Boiling point
511.1 · 511.1±50.0 °C(Predicted)
Density
1.386 · 1.386±0.06 g/cm3(Predicted)
storage temp.
2 · under inert gas (nitrogen or Argon) at 2-8°C
solubility
Soluble in ethanol and methan
form
powder
pka
7.5 · 7.50±0.40(Predicted)
color
White
Major Application
food and beverages

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS ClassificationNot Classified

Hazard information

Hazard Classes and CategoriesNot Classified

Safety data

PPE
Eyeshields, Gloves, type N95 (US)
wgk
WGK 2
hs_code
29329990
Signal word
Warning
Symbol(GHS)
GHS07
safety_code
24/25
Storage Class
11 - Combustible Solids
Hazard statements
H302-H315-H319-H335
Precautionary statements
P261-P305+P351+P338

Chemistry & industry

Pharmacology

Cellular LocationsMembrane
Applications · 2 items

DescriptionPinocembrin is a flavonoid that has been found in Eucalyptus, and has diverse biological activities. It induces apoptosis in, and inhibits the migration of, SKOV3 ovarian cancer cells when used at a concentration of 200 μM. Pinocembrin (5 mg/kg) reduces lesion volume, as well as brain microglial activation and production of IL-1β, IL-6, and TNF-α in a mouse model of collagenase-induced intracerebral hemorrhage (ICH). It prevents increases in plasma and kidney malondialdehyde (MDA) levels, glomeruli lobulation, mesangial expansion, and tubule vacuolization and occlusion, and it decreases hepatic cholesterol, triglyceride, and LDL levels in a rat model of diabetic nephropathy. Pinocembrin (20 and 50 mg/kg) reduces pulmonary edema, as well as neutrophil, lymphocyte, and macrophage infiltration in a mouse model of LPS-induced lung injury.

UsesPinocembrin is a flavanoid with antioxidant activity found in damiana, honey, and propolis. Recent studies show that Pinocembrin maybe be a therapeutic option in reducing cerebral ischemia/reperfusion injury as a result of its anti-oxidative and anti-apoptotic effects. Pinocembrin displayed neuroprotective effects in glutamate injury model partly by inhibiting p53 expression causing a lower Bax-Bcl-2 ratio and by inhibiting the release of cytochrome c.

Additional notes · 1 item

DefinitionChEBI: Pinocembrin is a dihydroxyflavanone in which the two hydroxy groups are located at positions 5 and 7. A natural product found in Piper sarmentosum and Cryptocarya chartacea. It has a role as an antioxidant, an antineoplastic agent, a vasodilator agent, a neuroprotective agent and a metabolite. It is a dihydroxyflavanone and a (2S)-flavan-4-one.

Related reactions

3 records
New reaction record
HRID 1948748 reaction equation
HRID 1948748As productuspto-grants-2013_03
HRID 1949179 reaction equation
HRID 1949179As reactantuspto-grants-2013_03
HRID 1949180 reaction equation
HRID 1949180As reactantuspto-grants-2013_03

Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
More actions
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DTXSID
DTXSID3075412
ChEMBL
CHEMBL399910
ChEBI
CHEBI:28157
UNII
8T7C8CH791
EC Number
817-146-3
Nikkaji
J12.347A
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/t13-/m0/s1
InChIKey
URFCJEUYXNAHFI-ZDUSSCGKSA-N
SMILES
OC1=C(C(C[C@@H](C2=CC=CC=C2)O3)=O)C3=CC(O)=C1
LogP
3.225 · 3.225 (est)
FDA UNII
8 T7C8CH791 · 8T7C8CH791
EPA Substance Registry System
4 H-1-Benzopyran-4-one, · 4H-1-Benzopyran-4-one, 2,3-dihydro-5,7-dihydroxy-2-phenyl-, (2S)- (480-39-7)
UNSPSC Code
41116107 · 41116107
NACRES
24 · NA.24
Symbol(GHS)
7 · GHS07
Signal word
Warning
Hazard statements
302 · H302-H315-H319-H335
Precautionary statements
261 · P261-P305+P351+P338
PPE
95 · Eyeshields, Gloves, type N95 (US)
Safety Statements
24 · 24/25
WGK Germany
2 · WGK 2
HS Code
29329990 · 29329990
Storage Class
11 · 11 - Combustible Solids