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(+)-Pinocembrin

HCID 68071
NotesReactions
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
DTXSID
DTXSID3075412
ChEMBL
CHEMBL399910
ChEBI
CHEBI:28157
UNII
8T7C8CH791
EC Number
817-146-3
Nikkaji
J12.347A

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
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

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.

Suppliers100 total

成都普瑞法科技开发有限公司+86-028-82633397 18982077548 · [email protected]
成都曼思特生物科技有限公司18010516991 · [email protected]
南京普怡生物科技有限公司13814510036 · [email protected]
成都埃法生物科技有限公司028-028-85142057 19983342022 · [email protected]
合肥翰刚医药科技有限公司+8618062405514 · [email protected]
成都健腾生物技术有限公司028-85159085 18080455027 · [email protected]
成都市久鼎化学技术有限公司18584079237 · [email protected]
上海如吉生物科技发展有限公司+86-21-65211385-8001 36031160 · [email protected]
上海晶抗生物工程有限公司021-54721350 13524668266 · [email protected]
大连美仑生物技术有限公司0411-62910999 13889544652 · [email protected]
南京圣亿来化工有限公司19951936396 · [email protected]
上海诗丹德标准技术服务有限公司021-021-57127007-6622-6622 17621252073 · [email protected]
成都普思生物科技股份有限公司028-85370565-229 18080489829 · [email protected]
成都普菲德生物技术有限公司028-82610909 13388174823 · [email protected]
上海融禾医药科技发展有限公司17301719108 13341702378 · [email protected]
武汉丰泰威远科技有限公司+86-27-8746-5837 +86-18627785180 · [email protected]
武汉丰泰威远科技有限公司027-87465837 19945049750 · [email protected]
贵州迪大科技有限责任公司0851-8475-2296 18096062265 · [email protected]
Aktin Chemicals, Inc.028-85159085 · [email protected]
云南西力生物技术股份有限公司0871-65217109 · [email protected]
上海源叶生物科技有限公司18916372613 · [email protected]
成都瑞芬思德丹生物科技有限公司2355253622; 18981954830 · [email protected]
上海倍卓生物科技有限公司021-61119791,13386096464 · [email protected]
上海楷树化学科技有限公司021-51987688-803 18916626396 · [email protected]
上海将来实业股份有限公司400-0066400 13621662912 · [email protected]
上海笛柏生物科技有限公司400-008-9730,021-54359730 400-008-9730 · [email protected]
雷丁试剂0510-85629785 18013409632 · [email protected]
上海卓因生物科技有限公司021-61317773 · [email protected]
南京恩德萨生物科技有限公司025-58862853 18915922038 · [email protected]
上海麦克林生化科技股份有限公司15221275939 15221275939 · [email protected]
杭州杰恒化工有限公司0571-87396432 · [email protected]
上海永叶生物科技有限公司86-021-61559134 15921386130 · [email protected]
南京多隆生物科技有限公司18905173768 · [email protected]
铜陵恒优生物科技有限公司021-50426030 13856289449;13124863828 · [email protected]
TargetMol中国(陶术生物)021-021-33632979 15002134094 · [email protected]
湖北康恩化学有限公司180-64105258 18064105258 · [email protected]
武汉天植生物技术有限公司18607101326 15172504745 · [email protected]
上海陶术生物科技股份有限公司+1-781-999-5354; +1-00000000000 · [email protected]
Wuhan ChemNorm Biotech Co.,Ltd.+86-27-8439 4403 18971486879 · [email protected]
上海珞珐生化科技有限公司021-51111890 15317326293 · [email protected]
EMMX Biotechnology LLC888-539-0666 · [email protected]
上海前衍生物科技有限公司02781293128 · [email protected]
上海西格生物科技有限公司021-57810052 18930344717 · [email protected]
众鑫辰实(武汉)科技有限公司18942922096 · [email protected]
南京博米尔生物科技有限公司025-83453382-8005 · [email protected]
Target molecule Corp.857-239-0968 · [email protected]
上海澄绍生物科技有限公司021-61847300 13341622919 · [email protected]
上海煜柯化学品有限公司13391486464 · [email protected]
上海新平精细化学品有限公司18221735425 · [email protected]
广东翁江化学试剂有限公司0751-2886750 13927877953 · [email protected]
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