Glycitein
Gycitein · GLYCITEIN · GLYCETEIN · Glicetein · Glycitein-RM · Glycitein(SH) · Glycitein, >=98% · Glycitein (15 mg)
Identifiers & Physical Properties
| CAS No. | 40957-83-3 |
|---|---|
| Molecular formula | C16H12O5 |
| Average molar mass | 284.26 g/mol |
| Monoisotopic mass | 284.06847348 g/mol |
| SMILES | COc1cc2c(=O)c(-c3ccc(O)cc3)coc2cc1O |
| InChIKey | DXYUAIFZCFRPTH-UHFFFAOYSA-N |
| PubChem CID | 5317750 |
| ChEMBL | CHEMBL513024 |
| ChEBI | CHEBI:34778 |
| DTXSID | DTXSID40193960 |
Chemical & Physical Properties
| XLogP | 2.4 |
|---|---|
| Topological polar surface area | 76 |
| Hydrogen bond donors | 2 |
| Hydrogen bond acceptors | 5 |
| Rotatable bonds | 2 |
| Heavy atoms | 21 |
| Formal charge | 0 |
| Complexity | 424 |
| Lipids | Polyketides [PK] -> Flavonoids [PK12] -> Isoflavonoids [PK1205] |
| LogP (partition coefficient) | 2.57 |
| Endocrine Disruptors | Potential endocrine disrupting compound |
| Physical Description | Solid |
| Melting point | >300°C |
| Boiling point | 547.4±50.0 °C(Predicted) |
| Density | 1.420±0.06 g/cm3(Predicted) |
| Storage conditions | -20°C |
| Solubility | Aqueous Base (Slightly), DMSO (Slightly) |
| pKa (acidity coefficient) | 7.03±0.20(Predicted) |
| Physical state | 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 (partition coefficient) | 2.570 (est) |
| CAS DataBase Reference | 40957-83-3(CAS DataBase Reference) |
| EWG's Food Scores | 1 |
| FDA UNII | 92M5F28TVF |
| UNSPSC Code | 85151701 |
| NACRES | NA.51 |
| GHS pictogram | GHS05,GHS06 |
| Signal word | Danger |
| GHS hazard statements | H301-H311-H314-H331 |
| GHS 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 |
| Personal protective equipment (PPE) | Eyeshields, Gloves, type N95 (US) |
| Hazard symbols | Xi |
| Safety statements (S) | 24/25 |
| Water hazard class (WGK) | 3 |
| Customs code | 29329990 |
| Storage class | 11 - Combustible Solids |
Safety & Regulations
| Regulatory information | 4H-1-Benzopyran-4-one, 7-hydroxy-3-(4-hydroxyphenyl)-6-methoxy-: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right. |
|---|---|
| Personal protective equipment (PPE) | Eyeshields, Gloves, type N95 (US) |
| Water hazard class (WGK) | 3 |
| Customs code | 29329990 |
| Signal word | Danger |
| GHS pictogram | GHS05,GHS06 |
| Hazard symbols | Xi |
| Safety statements (S) | 24/25 |
| Storage class | 11 - Combustible Solids |
| GHS hazard statements | H301-H311-H314-H331 |
| GHS 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 |
Applications & Uses
Description
Glycitein 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.
Uses
Glycitein 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).
Uses
Glycitein 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.
Uses
The compund shows an anti-cancer activity, plasma cholesterol reduction, reduction in postmenopausal bone loss
General Description
Glycitein is an isoflavone found in soy food products.