Robinin

HCID 5281693

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Basic information

CAS: 301-19-9
Standard SMILES: C[C@@H]1O[C@@H](OC[C@H]2O[C@@H](Oc3c(-c4ccc(O)cc4)oc4cc(O[C@@H]5O[C@@H](C)[C@H](O)[C@@H](O)[C@H]5O)cc(O)c4c3=O)[C@H](O)[C@@H](O)[C@H]2O)[C@H](O)[C@H](O)[C@H]1O
InChIKey: PEFASEPMJYRQBW-HKWQTAEVSA-N
Molecular formula: C33H40O19
Average molar mass: 740.7 g/mol
Monoisotopic mass: 740.21637906

Overview

Robinin is a glycosyloxyflavone that is kaempherol substituted by a 6-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-galactopyranosyl residue at position 3 and a 6-deoxy-alpha-L-mannopyranosyl residue at position 7 via a glycosidic linkage. It has a role as a plant metabolite. It is a dihydroxyflavone and a glycosyloxyflavone. It is functionally related to a kaempferol.

Names & identifiers

Preferred name: Robinin
IUPAC: 5-hydroxy-2-(4-hydroxyphenyl)-7-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-3-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-[[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-4-one
English name: Robinin
Molecular formula: C33H40O19
Molecular weight: 740.66

Names & synonyms

Robinin301-19-975RT1VGM60DTXSID401031393CHEBI:8878NSC-92224H-1-Benzopyran-4-one, 3-((6-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-galactopyranosyl)oxy)-7-((6-deoxy-alpha-L-mannopyranosyl)oxy)-5-hydroxy-2-(4-hydroxyphenyl)-5-hydroxy-2-(4-hydroxyphenyl)-7-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-3-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-[[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxymethyl]tetrahydropyran-2-yl]oxy-chromen-4-one5-hydroxy-2-(4-hydroxyphenyl)-7-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy-3-[(2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-[[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxymethyl]oxan-2-yl]oxychromen-4-one5-hydroxy-2-(4-hydroxyphenyl)-7-((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl)oxy-3-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl)oxymethyl)tetrahydropyran-2-yl)oxy-chromen-4-one5-hydroxy-2-(4-hydroxyphenyl)-7-((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl)oxy-3-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-(((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl)oxymethyl)oxan-2-yl)oxychromen-4-oneRefChem:179724

Show more names

Nsc9222Aids082734Robinin-RMAids-082734Robinin (Standard)Robinin >=90.0% (HPLC)KAEMPFEROL 3-ROBINOSIDE 7-RHAMNOSIDE

DTXCID101784927206-113-35-hydroxy-2-(4-hydroxyphenyl)-7-((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl)oxy-3-((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl)oxymethyl)oxan-2-yl)oxychromen-4-oneKaempferol-3-O-gal-rham-7-O-rhamEINECS 206-113-3Kaempferol-3-O-robinoside-7-O-rhamnosideNSC 9222UNII-75RT1VGM60

Database identifiers

CAS: 301-19-9
PubChem CID: 5281693
DTXSID: DTXSID401031393
ChEBI: CHEBI:8878
UNII: 75RT1VGM60
EC Number: 206-113-3
Nikkaji: J11.402B

Properties

Computed structural properties

XLogP: -2.2
Topological polar surface area: 304 Å²
Hydrogen bond donors: 11
Hydrogen bond acceptors: 19
Rotatable bonds: 8
Heavy atoms: 52
Formal charge: 0
Complexity: 1,260

Experimental & physicochemical properties

LipidsPolyketides [PK] -> Flavonoids [PK12] -> Flavones and Flavonols [PK1211]

Physicochemical properties

Melting point: 194 · 194-195°C
Boiling point: 1064.4 · 1064.4±65.0 °C(Predicted)
Density: 1.74 · 1.74±0.1 g/cm3(Predicted)
storage temp.: -20 °C · -20°C
solubility: Soluble in hot water
form: powder
pka: 5.81 · 5.81±0.40(Predicted)
color: light yellow crystal. hydrate: light yellow needles.
Water Solubility: soluble in hot water.
Major Application: food and beverages
InChIKey: PEFASEPMJYRQBW-HKWQTAEVSA-N
SMILES: C[C@@H]1O[C@@H](OC[C@H]2O[C@@H](OC3=C(Oc4cc(O[C@@H]5O[C@@H](C)[C@H](O)[C@@H](O)[C@H]5O)cc(O)c4C3=O)c6ccc(O)cc6)[C@H](O)[C@@H](O)[C@H]2O)[C@H](O)[C@H](O)[C@H]1O
LogP: 0.89 · 0.890 (est)
CAS DataBase Reference: 301 · 301-19-9
FDA UNII: 75 RT1VGM60 · 75RT1VGM60
UNSPSC Code: 41116107 · 41116107
NACRES: 24 · NA.24
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 302 · H302
Precautionary statements: 264 · P264-P270-P301+P312+P330-P501
Safety Statements: 22 · 22-24/25
WGK Germany: 3 · 3
Storage Class: 11 · 11 - Combustible Solids
Hazard Classifications: 4 Oral · Acute Tox. 4 Oral

Safety & regulation

GHS classification

GHS Classification · 4 items

Warning

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

P264, P270, P301+P317, P330, and P501 (click each P-code to see the statement)

The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

Hazard information

Hazard Classes and CategoriesAcute Tox. 4 (100%)

Safety data

wgk: 3
Signal word: Warning
Symbol(GHS): GHS07
safety_code: 22-24/25
Storage Class: 11 - Combustible Solids
Hazard statements: H302
Hazard Classifications: Acute Tox. 4 Oral
Precautionary statements: P264-P270-P301+P312+P330-P501

Chemistry & industry

Applications

Usesfood and beverages

Suppliers100 total

南京世洲生物科技有限公司025-85560043 15850508050 · [email protected]

成都普瑞法科技开发有限公司+86-028-82633397 18982077548 · [email protected]

南通飞宇生物科技有限公司0513-68819626 15152877458 · [email protected]

銘瑞集團有限公司17318633522 · [email protected]

成都埃法生物科技有限公司028-028-85142057 19983342022 · [email protected]

Additional notes · 1 item

DefinitionChEBI: Robinin is a glycosyloxyflavone that is kaempherol substituted by a 6-O-(6-deoxy-alpha-L-mannopyranosyl)-beta-D-galactopyranosyl residue at position 3 and a 6-deoxy-alpha-L-mannopyranosyl residue at position 7 via a glycosidic linkage. It has a role as a plant metabolite. It is a glycosyloxyflavone and a dihydroxyflavone. It is functionally related to a kaempferol.

Related reactions

1 records

New reaction record

HRID 61524As reactantuspto-grants-2016_09

Compound notes

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