Daidzein

Iupac Name：7-hydroxy-3-(4-hydroxyphenyl)chromen-4-one

Molecular Weight：254.241

Modify Date.: 2022-10-26 20:47

Introduction: Inactive 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) View more+

Request For Quotation

1. Names and Identifiers

1.1 Name: Daidzein
1.2 Synonyms: 4',7-Dihydroxyisoflavone 4,7-Dihydroxyisoflavone(Daidzein) 4’,7-dihydroxy-isoflavon 4H-1-Benzopyran-4-one, 7-hydroxy-3-(4-hydroxyphenyl)- 7,4'-dihydroxyisoflavone 7-Hydroxy-3-(4-hydroxy phenyl) chromone 7-Hydroxy-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one (7-Hydroxy-3-(4-hydroxyphenyl)chromone 7-Hydroxy-3-(4-hydroxyphenyl)-4H-chromen-4-one Daidsein DAIDZEIN, (AMERICAN HERBAL PHARMACOPOEIA) DAIDZEIN:4',7-DIHYDROXY ISOFLAVONE Daidzeol Daizeol EINECS 207-635-4 isoaurostatin K 251-6 k251b MFCD00016954 Soybean Extract Tatoin

1.3 CAS No.: 486-66-8

1.4 CID: 5281708

1.5 EINECS(EC#): 207-635-4

1.6 Molecular Formula: C15H10O4 (isomer)

1.7 Inchi: 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

1.8 InChkey: ZQSIJRDFPHDXIC-UHFFFAOYSA-N

1.9 Canonical Smiles: C1=CC(=CC=C1C2=COC3=C(C2=O)C=CC(=C3)O)O

1.10 Isomers Smiles: C1=CC(=CC=C1C2=COC3=C(C2=O)C=CC(=C3)O)O

2. Properties

2.1 Density: 1.443

2.1 Melting point: 315-323oC (dec.)

2.1 Boiling point: 512.8 °C at 760 mmHg

2.1 Refractive index: 1.698

2.1 Flash Point: 201.2 °C

2.1 Precise Quality: 254.05800

2.1 PSA: 70.67000

2.1 logP: 2.87120

2.1 Solubility: DMSO: 10?mg/mL

2.2 Appearance: white to off-white crystalline powder

2.3 Storage: Ambient temperatures.

2.4 Chemical Properties: Off-White Crystalline Solid

2.5 Color/Form: Powder

2.6 Physical: Solid

2.7 pKa: 7.01±0.20(Predicted)

2.8 Water Solubility: insoluble

2.9 Stability: Stable under normal shipping and handling conditions.

2.10 StorageTemp: 2-8°C

3. Use and Manufacturing

3.1 Definition: ChEBI: A member of the class of 7-hydroxyisoflavones that is 7-hydroxyisoflavone substituted by an additional hydroxy group at position 4'.

3.2 GHS Classification: Signal: Warning
GHS Hazard Statements
Aggregated GHS information provided by 36 companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Reported as not meeting GHS hazard criteria by 3 of 36 companies. For more detailed information, please visit ECHA C&L website

Of the 4 notification(s) provided by 33 of 36 companies with hazard statement code(s):

H315 (96.97%): Causes skin irritation [Warning Skin corrosion/irritation]
H319 (96.97%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

Precautionary Statement Codes
P264, P280, P302+P352, P305+P351+P338, P321, P332+P313, P337+P313, and P362

3.3 Usage: Inactive 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)

4. Safety and Handling

4.1 Symbol: GHS07;

4.1 Hazard Codes: Xi

4.1 Signal Word: Warning

4.1 Risk Statements: R36/38

4.1 Safety Statements: S26;S37/39

4.1 Hazard Class: IRRITANT

4.1 Hazard Declaration: H315; H319

4.1 RIDADR: 25kgs

4.1 Caution Statement: P280-P305 + P351 + P338-P337 + P313

4.1 WGK Germany: 3

4.1 RTECS: DJ3100040

4.1 Safety: Hazard Codes:?Xi
Risk Statements: 36/38
R36/38:Irritating to eyes and skin.
Safety Statements: 24-26-37/39
S24:Avoid contact with skin.?
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.?
S37/39:Wear suitable gloves and eye/face protection.
WGK Germany: 3
RTECS: DJ3100040

4.2 Specification: ? Daidzein , with CAS number of 486-66-8, can be called 4',7-dihydroxyisoflavone ; Cyproheptadine ; 4H-1-Benzopyran-4-one, 7-hydroxy-3-(4-hydroxyphenyl)- ; 7-Hydroxy-3-(4-hydroxyphenyl)-4-benzopyrone ; 7-hydroxy-3-(4-hydroxyphenyl)-4H-chromen-4-one ; 7,4-Dihydroxyisoflavone . Daidzein (CAS NO.486-66-8) is one of several known isoflavones, which are found in a number of plants and herbs like the Thai Kwao Krua or Pueraria Mirifica, but soybeans and soy products like tofu and textured vegetable protein are the primary food source. Soy isoflavones are a group of compounds found in and isolated from the soybean. Besides functioning as antioxidants, many isoflavones have been shown to interact with animal and human estrogen receptors, and are therefore known as phytoestrogens. Soy isoflavones also produce non-hormonal effects.

4.3 Toxicity

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
mouse	LD50	intraperitoneal	> 2gm/kg (2000mg/kg)	?	Pharmaceutical Chemistry Journal Vol. 13, Pg. 51, 1979.

View all

5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Skin irritation, Category 2

Eye irritation, Category 2

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Warning
Hazard statement(s)	H315 Causes skin irritation H319 Causes serious eye irritation
Precautionary statement(s)
Prevention	P264 Wash ... thoroughly after handling. P280 Wear protective gloves/protective clothing/eye protection/face protection.
Response	P302+P352 IF ON SKIN: Wash with plenty of water/... P321 Specific treatment (see ... on this label). P332+P313 If skin irritation occurs: Get medical advice/attention. P362+P364 Take off contaminated clothing and wash it before reuse. P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. P337+P313 If eye irritation persists: Get medical advice/attention.
Storage	none
Disposal	none

2.3 Other hazards which do not result in classification

none

View all

6. NMR Spectrum

13C NMR : Predict

1H NMR : Predict

Predict 1H proton NMR

7. Synthesis Route

486-66-8Total: 32 Synthesis Route

552-66-9 146 Suppliers

486-66-8 358 Suppliers

Literatures:
AMANO ENZYME INC. Patent: US2006/216281 A1, 2006 ; Location in patent: Page/Page column 9 ;
Yield: ~99%

486-63-5 2 Suppliers

486-66-8 358 Suppliers

Literatures:
Biegasiewicz, Kyle F.; Denis, Jeffrey D. St.; Carroll, Vincent M.; Priefer, Ronny Tetrahedron Letters, 2010 , vol. 51, # 33 p. 4408 - 4410
Yield: ~88%

485-72-3 279 Suppliers

486-66-8 358 Suppliers

Literatures:
Matin, Azadeh; Gavande, Navnath; Kim, Moon S.; Yang, Nancy X.; Salam, Noeris K.; Hanrahan, Jane R.; Roubin, Rebecca H.; Hibbs, David E. Journal of Medicinal Chemistry, 2009 , vol. 52, # 21 p. 6835 - 6850
Yield: ~66%

View all

8. Precursor and Product

precursor:

68-12-2

485-72-3

15485-80-0

22877-01-6

552-66-9

17720-60-4

131887-80-4

58822-01-8

2491-38-5

156-38-7

1157-39-7

531-95-3

95-01-2

486-63-5

1621-59-6

124590-31-4

56401-06-0

578-86-9

108-46-3

3682-01-7

148356-55-2

77316-78-0

140-53-4

View all

product :

62536-80-5

485-63-2

485-72-3

552-66-9

1041134-15-9

97846-18-9

1157-39-7

531-95-3

486-63-5

40957-83-3

17817-31-1

291759-05-2

852536-39-1

3682-01-7

21255-69-6

View all

9. Other Information

9.0 Description: Daidzein 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

9.1 Description: Daidzein is an isoflavone phytoestrogenic compound that has been found in soybeans and other legumes. It binds to estrogen receptor β (ERβ; K_i = 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 (K_is = 4.2 and 56 nM, respectively) over CAI, II, and IV (K_is = >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.

9.2 Physical properties: Appearance: pale-yellow prismatic crystal. Melting point: 315–323?°C. Solubility: soluble in ethanol and ether

9.3 History: Daidzein 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.

9.4 Indications: Daidzein is mainly used for the treatment of hypertension, coronary heart disease, cerebral thrombosis, and vertigo and aids in the treatment of sudden deafness. It can also treat women with menopause syndrome.

9.5 General Description: Daidzein 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.

9.6 Merck: 14,2801

9.7 BRN: 231523

9.8 Chemical Properties: Off-White Crystalline Solid

9.9 Uses: Inactive 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)

9.10 Uses: Daidzein 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

9.11 Uses: phytoestrogen

9.12 Definition: ChEBI: A member of the class of 7-hydroxyisoflavones that is 7-hydroxyisoflavone substituted by an additional hydroxy group at position 4'.

9.13 Biological Activity: Analog of the phytoestrogen genistein (5,7-Dihydroxy-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one ). Blocks G 1 phase cell cycle progression and is an agonist at estrogen receptors.

9.14 Usage: 4',7-Dihydroxyisoflavone is a phytoestrogen that is suggested to play a role in preventing hormone-induced cancers. It protects against oxidative damage in liver cells induced by 7,12-dimethylbenz[a]anthracene (DMBA). Catalase and superoxide dismutase activity, down-regulated by DMBA, was restored by daidzein.

9.15 Usage: Analog of genistein and an agonist at estrogen recpetors

10. Computational chemical data

Molecular Weight: 254.241g/mol
Molecular Formula: C₁₅H₁₀O₄
Compound Is Canonicalized: True
XLogP3-AA: 2.5
Exact Mass: 254.05790880
Monoisotopic Mass: 254.05790880
Complexity: 382
Rotatable Bond Count: 1
Hydrogen Bond Donor Count: 2
Hydrogen Bond Acceptor Count: 4
Topological Polar Surface Area: 66.8
Heavy Atom Count: 19
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADccBwOAAAAAAAAAAAAAAAAAAAAAAAAAAwYIAAAAAAAACBQAAAGgAACAAADASgmAIwBoAABgCIAqBSAAACCAAkIAAIiAEGCMgMJzaGNRqAcWAl4BUIuYeI7PzOIAAACAAIAABAAAAQABAAAAAAAAAAAA==

11. Recommended Suppliers

Global353SuppliersView all >>

Hebei Crovell Biotech Co. Ltd Diamond member

-120YR

Products:Cosmetic Raw Materials,solvents,etc.
Tel:86-311-66562153
Email:breeduan@crovellbio.com

Factory supply high purity CAS 486-66-8 Daidzein with fast delivery

Purity:99%Packing: 200kg/bag FOB
Price: 10 USD/kilogram
Time: 2023/06/06

Inquire

Wuhan Pharmchem Co., LTD. Diamond member

-121YR

Products:Pharma &Food Intermediates Water Treatment Chemicals Industrial Specialties Fine Chemicals
Tel:86-27-85835203
Email:steven@cspharmchem.com

Daidzein 98% 4',7-Dihydroxyisoflavone for health care EINECS 207-635-4

Purity:99%Packing: 200kg/bag FOB
Price: 140 USD/kg
Time: 2023/06/06

Inquire

Jinlan Pharm-Drugs Technology Co., Limited Diamond member

-112YR

Products:Veterinary products,Nutrition products,Agrochemicals,Active pharmaceutical Ingredients,Custom systhesis,Contract manufacturing
Tel:86-571-85829052
Email:market@royalpharms.com

Daidzein

Purity:99%Packing: 200kg/bag FOB
Price: 100 USD/kilogram
Time: 2023/05/31

Inquire

Shanghai Worldyang Chemical Co.,Ltd. Diamond member

-121YR

Products:API,intermediate,hormone
Tel:+86-21-56795766
Email:sales003@worldyachem.com

Daidzein 486-66-8

Purity:99%Packing: 200kg/bag FOB
Price:
Time: 2023/06/06

Inquire

Hangzhou ZeErRui Chemical Co., Ltd. Diamond member

-121YR

Products:We ZERchem, facing global High-tech pharmaceutical raw materials, high value-added new type intermediates fine chemicals custom synthesis, scale-up production and rare chemicals trade.
Tel:+86-571-82512721
Email:sales@zeerrui.com

Daidzein

Purity:99%Packing: 200kg/bag FOB
Price:
Time: 2023/06/06

Inquire

12. Realated Product Infomation

3682-01-7 Daidzein diacetate

291759-05-2 Daidzein-D6

1219803-57-2 Daidzein-d4

1179998-29-8 7,4'-Dibenzyl Daidzein

58970-69-7 Daidzein-4′-glucoside

53681-67-7 daidzein-4,7-diglucoside

38482-80-3 Daidzein-7-O-glucuronide

Recently Updated : 1616885-96-1 1617537-86-6 161912-04-5 1619977-74-0 162052-71-3 1620923-59-2 1621066-69-0 1621066-70-3 1621084-02-3 1621224-64-3