Basic information
- Standard SMILES
O=c1c(-c2ccc(O)cc2)coc2cc(O)ccc12- InChIKey
ZQSIJRDFPHDXIC-UHFFFAOYSA-N- Molecular formula
- C15H10O4
- Average molar mass
- 254.24 g/mol
- Monoisotopic mass
- 254.0579088
Overview
Daidzein is a member of the class of 7-hydroxyisoflavones that is 7-hydroxyisoflavone substituted by an additional hydroxy group at position 4'. It has a role as an EC 2.7.7.7 (DNA-directed DNA polymerase) inhibitor, an antineoplastic agent, an EC 3.2.1.20 (alpha-glucosidase) inhibitor, a plant metabolite and a phytoestrogen. It is a conjugate acid of a daidzein(1-).
Names & identifiers
- Preferred name
- Daidzein
- IUPAC
- 7-hydroxy-3-(4-hydroxyphenyl)chromen-4-one
- English name
- Daidzein
- Molecular formula
- C15H10O4
- Molecular weight
- 254.24
Names & synonyms
Show more names
Database identifiers
- CAS
486-66-8- PubChem CID
- 5281708
- DTXSID
DTXSID9022310- ChEMBL
CHEMBL8145- ChEBI
CHEBI:28197- UNII
- 6287WC5J2L
- EC Number
- 207-635-4
- Nikkaji
- J6.014C
Properties
Computed structural properties
- XLogP
- 2.5
- Topological polar surface area
- 66.8 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 1
- Heavy atoms
- 19
- Formal charge
- 0
- Complexity
- 382
Experimental & physicochemical properties
Collision Cross Section
155.8 Ų [M+H]+ [CCS Type: DT; Buffer gas: N2; Ionization: ESI+; Dataset: TOXCAST; Source Identifier: DTXSID9022310]
162.33 Ų [M-H]- [CCS Type: DT; Method: stepped-field]
172 Ų [M+Na]+
Physicochemical properties
- Melting point
- 315 · 315-323°C (dec.)
- Boiling point
- 317.45 °C · 317.45°C (rough estimate)
- Density
- 1.1629 · 1.1629 (rough estimate)
- refractive index
- 1.43 · 1.4300 (estimate)
- storage temp.
- 2 · 2-8°C
- solubility
- 10 mg/mL · DMSO: 10 mg/mL
- form
- Powder
- pka
- 7.01 · 7.01±0.20(Predicted)
- color
- White to off-white
- biological source
- synthetic
- Water Solubility
- insoluble
- Merck
- 14 · 14,2801
- BRN
- 231523 · 231523
- Major Application
- food and beverages
- Cosmetics Ingredients Functions
- SKIN CONDITIONING - MISCELLANEOUS
- InChI
- 1S/C15H10O4/c16-10-3-1-9(2-4-10)13-8-19-14-7-11(17)5-6-12(14)15(13)18/h1-8,16-17H
- InChIKey
- ZQSIJRDFPHDXIC-UHFFFAOYSA-N
- SMILES
- Oc1ccc(cc1)C2=COc3cc(O)ccc3C2=O
- LogP
- 2.632 · 2.632 (est)
- CAS DataBase Reference
- 486 · 486-66-8(CAS DataBase Reference)
- EWG's Food Scores
- 1 · 1
- NCI Dictionary of Cancer Terms
- daidzein
- FDA UNII
- 6287 WC5J2L · 6287WC5J2L
- EPA Substance Registry System
- 4 H-1-Benzopyran-4-one, · 4H-1-Benzopyran-4-one, 7-hydroxy-3-(4-hydroxyphenyl)- (486-66-8)
- UNSPSC Code
- 85151701 · 85151701
- NACRES
- 77 · NA.77
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
- Hazard statements
- 315 · H315-H319
- Precautionary statements
- 264 · P264-P280-P302+P352-P305+P351+P338-P332+P313-P337+P313
- Hazard Codes
- Xi
- Risk Statements
- 36 · 36/38
- Safety Statements
- 24 · 24-26-37/39
- WGK Germany
- 3 · 3
- RTECS
- 3100040 · DJ3100040
- HazardClass
- IRRITANT
- HS Code
- 29329990 · 29329990
- Storage Class
- 11 · 11 - Combustible Solids
- Hazard Classifications
- 2 Skin · Eye Irrit. 2Skin Irrit. 2
Safety & regulation
GHS classification
GHS Classification
This chemical does not meet GHS hazard criteria for 3.7% (3 of 81) of reports.
Warning
H315 (95.1%): Causes skin irritation [Warning Skin corrosion/irritation]
P264, P264+P265, P280, P302+P352, P305+P351+P338, P321, P332+P317, P337+P317, and P362+P364 (click each P-code to see the statement)
Aggregated GHS information provided per 81 reports by companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Toxicology
Safety data
- wgk
- 3
- rtecs
- DJ3100040
- hs_code
- 29329990
- risk_code
- 36/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- hazard_code
- Xi
- safety_code
- 24-26-37/39
- hazard_class
- IRRITANT
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H315-H319
- Hazard Classifications
- Eye Irrit. 2Skin Irrit. 2
- Precautionary statements
- P264-P280-P302+P352-P305+P351+P338-P332+P313-P337+P313
Chemistry & industry
Pharmacology
Uses & manufacturing
Uses
Isoflavones compounds are found in a number of plants, but soybeans and soy products like tofu and textured vegetable protein are the primary food source. Equol represents the main active product of daidzein metabolism, produced via specific microflora in the gut.
Applications
DescriptionDaidzein mainly comes from leguminous plants, the seeds of soybean (dadou), red clover grass, or all Pueraria roots. Its medicinal value was first recorded in Shen Nong Ben Cao Jing 2838 BC.Daidzein, one of the main soy isoflavones, is also the main component of radix puerariae (Gegen) which is the dry root of kudzu leguminous plants. Radix puerariae can reduce fever, produce saliva, and relieve diarrhea. Its chemical composition is complicated, including puerarin, xyloside, soy flavonoids, soybean flavonoid glycosides, beta-sitosterol, daidzin, daidzein. The main effective components are puerarin and daidzein
DescriptionDaidzein is an isoflavone phytoestrogenic compound that has been found in soybeans and other legumes. It binds to estrogen receptor β (ERβ; Ki = 2.8 μM) but not ERα at concentrations up to 1 mM. It is estrogenic in vitro, increasing gene transcription mediated by the estrogen response element (ERE) in a reporter assay in an ERβ-dependent manner (EC50 = 2.8 μM for MCF-7 cells expressing ERβ). Daidzein is an inhibitor of carbonic anhydrase (CA) that is selective for carbonic CAVII and CAXII (Kis = 4.2 and 56 nM, respectively) over CAI, II, and IV (Kis = >10,000, >10,000, and 718.7 nM, respectively). It reduces tumor growth in a PC3 prostate cancer mouse orthotopic model when administered at a dose of 50 mg/kg per day and potentiates the effects of radiation therapy.
HistoryDaidzein is a kind of isoflavone compound, which was first synthetized by researchers in China. It has been widely used in drugs, food supplements, and cosmetics. Because of two phenolic hydroxyl structures, Daidzein has poor water solubility, poor liposolubility, and strong first-pass effect, leading to the low bioavailability of oral absorption, which limits its widely clinical usage. Ipriflavone is a kind of isoflavone modified from Daidzein, which has been used for the treatment of osteoporosis in Japan and some European countries. The effects of a series of amino alkoxy derivatives of ipriflavones on inhibiting the bone absorption were evaluated. The researchers found that 7-amino alkoxy derivative works best. When Daidzein was alkylated or acylated at 7-hydroxyl selectively, the stability was increased, and thus the proliferation of MCF-7 cell was inhibited.
UsesInactive analog of Genistein (Cat. #G350000). Blocks the G1 phase of the cell cycle in Swiss 3T3 cells by inhibiting casein kinase II activity1. Daidzein has also been shown to inhibit the action of GABA on recombinant GABAA receptors2. uv max:250 nm (log e 4.44)
Usesphytoestrogen
UsesDaidzein belongs to the group of isoflavones. Daidzein and other isoflavone compounds, such as genistein, are present in a number of plants and herbs. Soy isoflavones are a group of compounds found in and isolated from the soybean. Besides functioning as
General DescriptionDaidzein is an endocrine-active estrogenic isoflavone. This phytoestrogen is capable to bind to estrogen to exert estrogenic effects in vivo. It can naturally be found in soybean seed and flour.
Upstream & downstream products
Upstream raw materials
Downstream products
Suppliers50 total
Additional notes
DefinitionChEBI: A member of the class of 7-hydroxyisoflavones that is 7-hydroxyisoflavone substituted by an additional hydroxy group at position 4'.
Related reactions
Linked notes
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