Basic information
- CAS
28608-75-5- Standard SMILES
O=c1cc(-c2ccc(O)c(O)c2)oc2c([C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)c(O)cc(O)c12- InChIKey
PLAPMLGJVGLZOV-VPRICQMDSA-N- Molecular formula
- C21H20O11
- Average molar mass
- 448.4 g/mol
- Monoisotopic mass
- 448.10056146
Overview
Orientin is a C-glycosyl compound that is luteolin substituted by a beta-D-glucopyranosyl moiety at position 8. It has a role as an antioxidant and a metabolite. It is a C-glycosyl compound, a 3'-hydroxyflavonoid and a tetrahydroxyflavone. It is functionally related to a luteolin.
Names & identifiers
- Preferred name
- Orientin
- IUPAC
- 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-8-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]chromen-4-one
- English name
- ORIENTIN
- Molecular formula
- C21H20O11
- Molecular weight
- 448.38
Names & synonyms
Orientin28608-75-5LutexinLuteolin 8-C-glucosideLuteolin-8-glucosideLuteolin-8-C-glucosideOrientine4H-1-Benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-8-beta-D-glucopyranosyl-5,7-dihydroxy-8-beta-D-glucosylluteolinIAX93XCW6CLuteolin 8-C-beta-D-glucopyranosideJ17.734B
Show more names
PolygoninLuteolin 8-C-β-D-glucopyranosideAids026706Aids-026706ORIENTIN(P)ORIENTIN,NA
2-(3,4-Dihydroxyphenyl)-8-beta-D-glucopyranosyl-5,7-dihydroxy-4H-1-benzopyran-4-oneMASSBANK PR020063CHEBI:7781DTXSID60182790C101142-(3,4-dihydroxyphenyl)-5,7-dihydroxy-8-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]chromen-4-one2-(3,4-dihydroxyphenyl)-8-beta-D-glucopyranosyl-5,7-dihydroxy-4H-chromen-4-one2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-8-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)chromen-4-one
Database identifiers
- CAS
28608-75-5- PubChem CID
- 5281675
Properties
Computed structural properties
- XLogP
- -0.2
- Topological polar surface area
- 197 Ų
- Hydrogen bond donors
- 8
- Hydrogen bond acceptors
- 11
- Rotatable bonds
- 3
- Heavy atoms
- 32
- Formal charge
- 0
- Complexity
- 729
Experimental & physicochemical properties
LipidsPolyketides [PK] -> Flavonoids [PK12] -> Flavones and Flavonols [PK1211]
Endocrine DisruptorsPotential endocrine disrupting compound
Physicochemical properties
- Melting point
- 260 · 260-285°C
- Boiling point
- 816.1 · 816.1±65.0 °C(Predicted)
- Density
- 1.759 · 1.759±0.06 g/cm3(Predicted)
- storage temp.
- 2 · 2-8°C(protect from light)
- solubility
- 1 M · 1 M NaOH: soluble1mg/mL, clear, yellow-orange
- pka
- 6.24 · 6.24±0.40(Predicted)
- form
- powder
- color
- yellow
- Stability
- Hygroscopic
- Major Application
- metabolomicsvitamins, nutraceuticals, and natural products
- InChIKey
- PLAPMLGJVGLZOV-FYNBPVOANA-N
Safety & regulation
GHS classification
GHS ClassificationNot Classified
Hazard information
Hazard Classes and CategoriesNot Classified
Safety data
- wgk
- 3
- rtecs
- DJ3009300
- hs_code
- 29389090
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- safety_code
- 24/25
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H302-H315-H319-H335
- Precautionary statements
- P261-P280-P301+P312-P302+P352-P305+P351+P338
Chemistry & industry
Applications
DescriptionOrientin is a flavone glycoside originally isolated from P. orientale that has diverse biological activities, including antioxidant, antibacterial, and anti-inflammatory properties. Orientin scavenges 2,2-diphenyl-1-picryl-hydrazyl (DPPH; ) radicals with an IC50 value of 316.21 μg/ml. It also decreases the cytopathic effects of parainfluenza type 3 virus with an IC50 value of 11.7 μg/ml and a cytotoxic concentration (CC50) value of 375 μg/ml in Hep-2 cells. Orientin (5-40 μM) inhibits LPS-induced barrier disruption, decreases the expression of toll-like receptor 4 (TLR4), phosphorylated p38, and NF-κB, and decreases TNF-α production and IL-6 secretion in a dose-dependent manner in human umbilical vein endothelial cells (HUVECs). It also prolongs survival in a mouse model of LPS-induced lethal endotoxemia when administered at a dose of 36 μg/animal 12 hours after LPS administration.
UsesOrientin is a flavone, a chemical flavonoid compound. Orientin have been investigated for its anti-oxidant, antihypertensive and antihyperlipidemic effects.
Suppliers19 total
成都普瑞法科技开发有限公司+86-028-82633397 18982077548 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
南通飞宇生物科技有限公司0513-68819626 15152877458 · [email protected]
成都普睿法药物研发有限公司82633860 18982077548 · [email protected]
上海迈瑞尔生化科技有限公司4006356688 18621169109 · [email protected]
大连美仑生物技术有限公司0411-62910999 13889544652 · [email protected]
上海融禾医药科技发展有限公司17301719108 13341702378 · [email protected]
Related reactions
1 records
Compound notes
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