Basic information
- Standard SMILES
COc1cc2c(=O)c(-c3ccc(O)cc3)coc2cc1O- InChIKey
DXYUAIFZCFRPTH-UHFFFAOYSA-N- Molecular formula
- C16H12O5
- Average molar mass
- 284.26 g/mol
- Monoisotopic mass
- 284.06847348
Overview
Glycitein is a methoxyisoflavone that is isoflavone substituted by a methoxy group at position 6 and hydroxy groups at positions 7 and 4'. It has been isolated from the mycelia of the fungus Cordyceps sinensis. It has a role as a plant metabolite, a fungal metabolite and a phytoestrogen. It is a 7-hydroxyisoflavone and a methoxyisoflavone. It is functionally related to an isoflavone.
Names & identifiers
- Preferred name
- Glycitein
- IUPAC
- 7-hydroxy-3-(4-hydroxyphenyl)-6-methoxychromen-4-one
- English name
- Glycitein
- Molecular formula
- C16H12O5
- Molecular weight
- 284.26
Names & synonyms
Show more names
Database identifiers
- CAS
40957-83-3- PubChem CID
- 5317750
- DTXSID
DTXSID40193960- ChEMBL
CHEMBL513024- ChEBI
CHEBI:34778- UNII
- 92M5F28TVF
- Nikkaji
- J17.583H
Properties
Computed structural properties
- XLogP
- 2.4
- Topological polar surface area
- 76 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 2
- Heavy atoms
- 21
- Formal charge
- 0
- Complexity
- 424
Experimental & physicochemical properties
Physicochemical properties
- Melting point
- 300 °C · >300°C
- Boiling point
- 547.4 · 547.4±50.0 °C(Predicted)
- Density
- 1.42 · 1.420±0.06 g/cm3(Predicted)
- storage temp.
- -20 °C · -20°C
- solubility
- Aqueous Base (Slightly), DMSO (Slightly)
- pka
- 7.03 · 7.03±0.20(Predicted)
- form
- Solid
- color
- Light Brown
- biological source
- synthetic (organic)
- InChI
- InChI=1S/C16H12O5/c1-20-15-6-11-14(7-13(15)18)21-8-12(16(11)19)9-2-4-10(17)5-3-9/h2-8,17-18H,1H3
- InChIKey
- DXYUAIFZCFRPTH-UHFFFAOYSA-N
- SMILES
- C1OC2=CC(O)=C(OC)C=C2C(=O)C=1C1=CC=C(O)C=C1
- LogP
- 2.57 · 2.570 (est)
- CAS DataBase Reference
- 40957 · 40957-83-3(CAS DataBase Reference)
- EWG's Food Scores
- 1 · 1
- FDA UNII
- 92 M5F28TVF · 92M5F28TVF
- UNSPSC Code
- 85151701 · 85151701
- NACRES
- 51 · NA.51
- Symbol(GHS)
- 5 · GHS05,GHS06
- Signal word
- Danger
- Hazard statements
- 301 · H301-H311-H314-H331
- Precautionary statements
- 260 · P260-P264-P270-P271-P280-P301+P330+P331-P302+P352-P303+P361+P353-P304+P340-P305+P351+P338-P310-P403+P233-P405-P501
- PPE
- 95 · Eyeshields, Gloves, type N95 (US)
- Hazard Codes
- Xi
- Safety Statements
- 24 · 24/25
- WGK Germany
- 3 · 3
- HS Code
- 29329990 · 29329990
- Storage Class
- 11 · 11 - Combustible Solids
Safety & regulation
Hazard information
Safety data
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 3
- hs_code
- 29329990
- Signal word
- Danger
- Symbol(GHS)
- GHS05,GHS06
- hazard_code
- Xi
- safety_code
- 24/25
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H301-H311-H314-H331
- Precautionary statements
- P260-P264-P270-P271-P280-P301+P330+P331-P302+P352-P303+P361+P353-P304+P340-P305+P351+P338-P310-P403+P233-P405-P501
Chemistry & industry
Pharmacology
Applications
DescriptionGlycitein is an O-methylated isoflavone that comprises 5-10% of the total isoflavones in soy food products. This phytoestrogen is reported to have weak estrogenic activity, displacing estradiol binding at the estrogen receptor in vitro with an IC50 value of 3.94 μM. It suppresses the proliferation of osteoblasts and promotes differentiation from its progenitor. It has also been used to attenuate proliferation (10 μM) of aortic smooth muscle cells related to atherosclerotic vascular change in stroke-prone hypertensive rats and to protect against beta amyloid (Aβ)-induced toxicity and oxidative stress (100 μg/ml) in C. elegans expressing human Aβ.
UsesGlycitein may be used as a reference standard in the determination of glycitein in hydrolyzed dry soya extracts using reversed-phase high-performance liquid chromatography (RP-HPLC).
UsesGlycitein has been used as standard for the analysis of soy isoflavones and metabolites in urine. It has also been used to bind to recombinant estrogen and progesterone receptors to know the relative binding affinity (RBA) for detection of potential endocrine disruptors.
UsesThe compund shows an anti-cancer activity, plasma cholesterol reduction, reduction in postmenopausal bone loss
General DescriptionGlycitein is an isoflavone found in soy food products.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers50 total
Additional notes
DefinitionChEBI: A methoxyisoflavone that is isoflavone substituted by a methoxy group at position 6 and hydroxy groups at positions 7 and 4'. It has been isolated from the mycelia of the fungus Cordyceps sinensis.
Related reactions
Linked notes
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