Basic information
- CAS
4261-42-1- Standard SMILES
O=c1cc(-c2ccc(O)c(O)c2)oc2cc(O)c([C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)c(O)c12- InChIKey
ODBRNZZJSYPIDI-VJXVFPJBSA-N- Molecular formula
- C21H20O11
- Average molar mass
- 448.4 g/mol
- Monoisotopic mass
- 448.10056146
Overview
Isoorientin is a flavone C-glycoside consisting of luteolin having a beta-D-glucosyl residue at the 6-position. It has a role as an antineoplastic agent and a radical scavenger. It is a tetrahydroxyflavone and a flavone C-glycoside. It is functionally related to a luteolin. It is a conjugate acid of an isoorientin(1-).
Names & identifiers
- Preferred name
- Isoorientin
- IUPAC
- 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-6-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]chromen-4-one
- English name
- HOMOORIENTIN
- Molecular formula
- C21H20O11
- Molecular weight
- 448.38
Names & synonyms
IsoorientinHomoorientin4261-42-1iso-orientinLespecapitioside6-Glc-luteolinLUTONARETINCHEBI:17965A37342TIX1DTXSID509626094H-1-Benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-6-beta-D-glucopyranosyl-5,7-dihydroxy-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-6-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]chromen-4-one
Show more names
2-(3,4-Dihydroxyphenyl)-6-β-D-glucopyranosyl-5,7-dihydroxy-4H-1-benzopyran-4-oneIsoorientinIHomoorientin(P)Homoorientin-RMlespecapittosideHOMOORIENTIN hplcHOMOORIENTIN WITH HPLC
(1S)-1,5-anhydro-1-[2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-6-yl]-D-glucitol(1S)-1,5-anhydro-1-(2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4H-chromen-6-yl)-D-glucitol2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-6-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)chromen-4-oneRefChem:40050DTXCID6013904062-(3,4-dihydroxyphenyl)-5,7-dihydroxy-6-((2S,4S,5S)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl)chromen-4-oneLuteolin-6-C-glucosideLuteolin 6-C-glucoside
Database identifiers
- CAS
4261-42-1- PubChem CID
- 114776
- DTXSID
DTXSID50962609- ChEMBL
CHEMBL239559- ChEBI
CHEBI:17965- UNII
- A37342TIX1
- EC Number
- 610-045-3
- Nikkaji
- J14.555F
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]
Physicochemical properties
- Melting point
- 245 · 245-246°C
- Boiling point
- 856.7 · 856.7±65.0 °C(Predicted)
- Density
- 1.759 · 1.759±0.06 g/cm3(Predicted)
- storage temp.
- 2 · 2-8°C
- solubility
- 5 mg/mL, · methanol: soluble5mg/mL, clear, colorless to yellow
- form
- powder
- pka
- 5.9 · 5.90±0.40(Predicted)
- color
- yellow
- biological source
- leaves (Phyllostachya Nigra)
- Stability
- Hygroscopic
- Major Application
- food and beverages
- InChIKey
- ODBRNZZJSYPIDI-VJXVFPJBSA-N
- SMILES
- C1(C(O)=CC2OC(C3C=CC(O)=C(O)C=3)=CC(=O)C=2C=1O)[C@H]1[C@H](O)[C@H]([C@H](O)[C@@H](CO)O1)O |&1:21,22,24,25,27,r|
- LogP
- 1.58 · 1.580 (est)
- FDA UNII
- 37342 TIX1 · A37342TIX1
- UNSPSC Code
- 85151701 · 85151701
- NACRES
- 25 · NA.25
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 302 · H302-H315-H319-H335
- Precautionary statements
- 261 · P261-P305+P351+P338
- Safety Statements
- 24 · 24/25
- WGK Germany
- 3 · 3
- HS Code
- 29389090 · 29389090
- Storage Class
- 11 · 11 - Combustible Solids
Safety & regulation
GHS classification
GHS Classification
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
Hazard Classes and CategoriesNot Classified
Safety data
- wgk
- 3
- 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-P305+P351+P338
Chemistry & industry
Applications
UsesReference Standard in the analysis of herbal medicinal products
UsesIsoorientin is a flavonoid compound that can be isolated from the passion flower, and several other species of plants. Isoorientin has also shown to exert antioxidant, anti-nociceptive, anti-inflammat ory and gastroprotective activities in several studies.
General DescriptionProduced and qualified by HWI pharma services GmbH.Exact content by quantitative NMR can be found on the certificate.
Suppliers100 total
北京华美互利生物化工010-56205725 · [email protected]
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Additional notes
DefinitionChEBI: A flavone C-glycoside consisting of luteolin having a beta-D-glucosyl residue at the 6-position.
Related reactions
1 records
Compound notes
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