1,3,6-Tri-O-Galloyl-Beta-D-Glucose
Basic information
- CAS
18483-17-5- Standard SMILES
O=C(OC[C@H]1O[C@@H](OC(=O)c2cc(O)c(O)c(O)c2)[C@H](O)[C@@H](OC(=O)c2cc(O)c(O)c(O)c2)[C@@H]1O)c1cc(O)c(O)c(O)c1- InChIKey
RNKMOGIPOMVCHO-SJMVAQJGSA-N- Molecular formula
- C27H24O18
- Average molar mass
- 636.5 g/mol
- Monoisotopic mass
- 636.09626391
Overview
Gallotannin is a class of hydrolysable tannins obtained by condensation of the carboxy group of gallic acid (and its polymeric derivatives) with the hydroxy groups of a monosaccharide (most commonly glucose). It is functionally related to a gallic acid.
Names & identifiers
- Preferred name
- 1,3,6-Tri-O-Galloyl-Beta-D-Glucose
- IUPAC
- [(2R,3R,4S,5R,6S)-3,5-dihydroxy-4,6-bis[(3,4,5-trihydroxybenzoyl)oxy]oxan-2-yl]methyl 3,4,5-trihydroxybenzoate
- English name
- 1,3,6-Tri-O-galloyl-β-D-glucose
- Molecular formula
- C27H24O18
- Molecular weight
- 636.47
Names & synonyms
18483-17-51,3,6-tri-O-galloyl-beta-D-glucoseCHEBI:24182[(2R,3R,4S,5R,6S)-3,5-dihydroxy-4,6-bis[(3,4,5-trihydroxybenzoyl)oxy]oxan-2-yl]methyl 3,4,5-trihydroxybenzoate((2R,3R,4S,5R,6S)-3,5-dihydroxy-4,6-bis((3,4,5-trihydroxybenzoyl)oxy)oxan-2-yl)methyl 3,4,5-trihydroxybenzoateRefChem:634117(2,3-dihydroxy-5-((3,4,5,6-tetrakis((3,4-dihydroxy-5-(3,4,5-trihydroxybenzoyl)oxybenzoyl)oxy)oxan-2-yl)methoxycarbonyl)phenyl) 3,4,5-trihydroxybenzoateGallotannin1,3,6-Tri-O-galloyl-b-D-glucose1,3,6-tri-o-galloylglucose1,3,6-Trigalloylglucose1,3,6-Tri-O-galloyl-b-D-glucopyranose
Show more names
1,3,6-Tri-O-galloyl-β-D-glucoseNSC 69861NP 005114Tannic acid (Corilagin)1,3,6-Tri-O-galloyl glucose1,3,6-Trigalloyl β-D-glucose1,3,6-Trigalloyl -β-D-glucose1,3,6-tris(3,4,5-trihydroxyben1,3,6-Trigalloyl β-D-glucose-RM
(2S,3R,4S,5R,6R)-3,5-Dihydroxy-6-(((3,4,5-trihydroxybenzoyl)oxy)methyl)tetrahydro-2H-pyran-2,4-diyl bis(3,4,5-trihydroxybenzoate)UNII-O8718334XJ1,3,6-tri-o-galloyl-beta-d-glucopyranoseO8718334XJ1,3,6-Trigalloyl glucosebeta-D-Glucopyranose 1,3,6-trigallateGlucopyranose, 1,3,6-trigallate, beta-D-beta-D-Glucopyranose, 1,3,6-tris(3,4,5-trihydroxybenzoate)
Properties
Computed structural properties
- XLogP
- 0.4
- Topological polar surface area
- 311 Ų
- Hydrogen bond donors
- 11
- Hydrogen bond acceptors
- 18
- Rotatable bonds
- 10
- Heavy atoms
- 45
- Formal charge
- 0
- Complexity
- 1,010
Physicochemical properties
- Melting point
- 167 ℃ · 167℃
- Boiling point
- 1103.6 · 1103.6±65.0 °C(Predicted)
- Density
- 1.98 · 1.98
- storage temp.
- -20 °C · -20°C
- pka
- 8.37 · 8.37±0.15(Predicted)
- form
- Solid
- color
- White to off-white
- BRN
- 76215 · 76215
- Major Application
- metabolomicsvitamins, nutraceuticals, and natural products
- InChIKey
- RNKMOGIPOMVCHO-SJMVAQJGSA-N
- SMILES
- O=C(C1=CC(O)=C(O)C(O)=C1)O[C@H]2[C@H](O)[C@@H](OC(C3=CC(O)=C(O)C(O)=C3)=O)[C@H](O)[C@@H](COC(C4=CC(O)=C(O)C(O)=C4)=O)O2
- FDA UNII
- 8718334 XJ · O8718334XJ
- UNSPSC Code
- 12352200 · 12352200
- NACRES
- 25 · NA.25
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
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 Classification
Warning
H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 2 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazard Classes and CategoriesSkin Irrit. 2 (100%)
Safety data
- wgk
- 3
- hs_code
- 29400090
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Storage Class
- 11 - Combustible Solids
- target organs
- Respiratory system
- Hazard statements
- H315-H319-H335
- Hazard Classifications
- Eye Irrit. 2Skin Irrit. 2STOT SE 3
- Precautionary statements
- P261-P264-P271-P280-P302+P352-P305+P351+P338
Chemistry & industry
Applications
Uses1,3,6-Trigalloylglucose is a tannin obtained from Picrorhiza kurroa seeds which exhibit lipid peroxidation and cyclooxygenase inhibitory activity.
Additional notes
DefinitionChEBI: Gallotannin is a class of hydrolysable tannins obtained by condensation of the carboxy group of gallic acid (and its polymeric derivatives) with the hydroxy groups of a monosaccharide (most commonly glucose). It is functionally related to a gallic acid.
Related reactions
0 records
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Compound notes
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