Basic information
- CAS
41001-90-5- Standard SMILES
COc1ccc([C@@H]2CC(=O)c3c(O)cc(O)cc3O2)cc1O- InChIKey
AIONOLUJZLIMTK-AWEZNQCLSA-N- Molecular formula
- C16H14O6
- Average molar mass
- 302.28 g/mol
- Monoisotopic mass
- 302.07903817
Overview
Hesperetin is a trihydroxyflavanone having the three hydroxy gropus located at the 3'-, 5- and 7-positions and an additional methoxy substituent at the 4'-position. It has a role as an antioxidant, an antineoplastic agent and a plant metabolite. It is a member of 4'-methoxyflavanones, a monomethoxyflavanone, a trihydroxyflavanone and a member of 3'-hydroxyflavanones. It is a conjugate acid of a hesperetin(1-).
Names & identifiers
- Preferred name
- Hesperetin
- IUPAC
- (2S)-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-2,3-dihydrochromen-4-one
- English name
- HESPERETIN
- Molecular formula
- C16H14O6
- Molecular weight
- 302.28
Names & synonyms
hesperetinHesperitin520-33-23',5,7-Trihydroxy-4'-methoxyflavanone(-)-hesperetin5,7,3'-Trihydroxy-4'-methoxyflavanone(2S)-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-2,3-dihydrochromen-4-one(-)-(S)-hesperetinEriodictyol 4'-monomethyl etherFEMA NO. 4313NSC-57654Q9Q3D557F1
Show more names
3',5,7-TRIHYDROXY-4-METHOXYFLAVANONEHESPERETINEHESPERETIN USP/EP/BP(+/-)-3',5,7-TRIHYDROXY-4'-METHOXYFLAVANONE2,3-DIHYDRO-5,7-DIHYDROXY-2S-(3-HYDROXY-4-METHOXPHENYL)-4H-1-BENZOPYRAN-4-ONE
4H-1-Benzopyran-4-one, 2,3-dihydro-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-, (S)-DTXSID4022319Flavanone, 3',5,7-trihydroxy-4'-methoxy-CHEBI:28230(S)-2,3-dihydro-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-4H-1-benzopyran-4-one4H-1-Benzopyran-4-one, 2,3-dihydro-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-, (2S)-2,3-DIHYDRO-5,7-DIHYDROXY-2-(3-HYDROXY-4-METHOXYPHENYL)-4H-1-BENZOPYRAN-4-ONERefChem:783778
Database identifiers
- CAS
41001-90-5、520-33-2- PubChem CID
- 72281
- DTXSID
DTXSID4022319- ChEMBL
CHEMBL399121- ChEBI
CHEBI:28230- UNII
- Q9Q3D557F1
- EC Number
- 208-290-2、805-255-9
- Nikkaji
- J9.235E
Properties
Computed structural properties
- XLogP
- 2.4
- Topological polar surface area
- 96.2 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 2
- Heavy atoms
- 22
- Formal charge
- 0
- Complexity
- 413
Experimental & physicochemical properties
Drugs
Pharmaceuticals -> Listed in ZINC15
Pharmaceuticals -> Metabolite of Hesperidin
LipidsPolyketides [PK] -> Flavonoids [PK12] -> Flavanones [PK1214]
LogP
2.60
2.6
Food AdditivesFLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Flavoring AgentsEU Flavoring substances
Endocrine DisruptorsPotential endocrine disrupting compound
Melting Point227.5 °C
Physical DescriptionSolid
Collision Cross Section
175.82 Ų [M+K]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
184.45 Ų [M+Na]+ [CCS Type: DT; Method: stepped-field]
169.1 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
177.9 Ų [M-H]-
Physicochemical properties
- storage temp.
- 2 · 2-8°C
- WGK Germany
- 3 · 3
Safety & regulation
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 97.9% (92 of 94) of all reports.
Not Classified
Aggregated GHS information provided per 94 reports by companies from 3 notifications to the ECHA C&L Inventory.
This chemical does not meet GHS hazard criteria for 100% (2 of 2) of all reports.
Not Classified
Aggregated GHS information provided per 2 reports by companies from 1 notifications to the ECHA C&L Inventory.
Hazard information
Regulatory Information
Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)
4H-1-Benzopyran-4-one, 2,3-dihydro-5,7-dihydroxy-2-(3-hydroxy-4-methoxyphenyl)-, (2S)-: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
Hazard Classes and Categories
Not Classified
Not Classified
Safety data
- wgk
- 3
Chemistry & industry
Pharmacology
Pharmacodynamics
Hesperetin is a cholesterol lowering flavanoid found in a number of citrus juices. It appears to reduce cholesteryl ester mass and inhibit apoB secretion by up to 80%. Hesperetin may have antioxidant, anti-inflammatory, anti-allergic, hypolipidemic, vasoprotective and anticarcinogenic actions.
Mechanism of Action
Hesperetin reduces or inhibits the activity of acyl-coenzyme A:cholesterol acyltransferase genes (ACAT<sub>1</sub> and ACAT<sub>2</sub>) and it reduces microsomal triglyceride transfer protein (MTP) activity. Hesperetin also seems to upregulate the LDL receptor. This leads to the reduced assembly and secretion of apoB-containing lipoproteins and enhanced reuptake of those lipoproteins, thereby lowering cholesterol levels.
Metabolism/MetabolitesHesperetin has known human metabolites that include Hesperetin 7-O-glucuronide and Hesperetin 3p-O-glucuronide.
Cellular LocationsMembrane
Suppliers22 total
北京华美互利生物化工010-56205725 · [email protected]
西安康培基生物科技有限公司86-029-85456576 · [email protected]
陕西新阳禾生物科技有限公司13991035447 · [email protected]
湖北源梦生物科技有限公司027-68897569 18120462897 · [email protected]
陕西新天域生物科技有限公司18165211053 · [email protected]
湖北源梦生物科技有限公司027-68897569 18120462897 · [email protected]
陕西缔都医药化工有限公司+86-29-81139210 +86-17392587031 · [email protected]
BOC Sciences[email protected]
Shanghai Acmec Biochemical Technology Co., Ltd.+86-18621343501 · [email protected]
郑州艾克姆化工有限公司037163312495 13303845143 · [email protected]
上海吉至生化科技有限公司021-4009004166/18616739031 18616739031 · [email protected]
深圳聚合生化科技有限公司+86-400-002-6226 · [email protected]
ANHUI WITOP BIOTECH CO., LTD+8618071025641 · [email protected]
XIAMEN AMITY INDUSTRY AND TRADE CO., LTD.+8618950047208 · [email protected]
SHANGHAI KEAN TECHNOLOGY CO., LTD.+8613817748580 · [email protected]
山东唐正生物科技有限公司15318846974
西安明朗生物科技有限公司18165366593 18729593924
上海同田生物技术有限公司021-51320588 · [email protected]
陕西新天域生物科技有限公司029-32565555 18690085745 · [email protected]
江苏多阳生物工程科技有限公司15161148838 · [email protected]
Hefei TNJ Chemical Industry Co.,Ltd.+86-0551-65418671 +86-189 4982 3763 · [email protected]
陕西新天域生物科技有限公司17749282610 17749282610 · [email protected]
Additional notes
DefinitionChEBI: Hesperetin is a trihydroxyflavanone having the three hydroxy gropus located at the 3'-, 5- and 7-positions and an additional methoxy substituent at the 4'-position. It has a role as an antioxidant, an antineoplastic agent and a plant metabolite. It is a monomethoxyflavanone, a trihydroxyflavanone, a member of 3'-hydroxyflavanones and a member of 4'-methoxyflavanones. It is a conjugate acid of a hesperetin(1-).
Related reactions
1 records
Compound notes
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