Daidzein

Modify Date: 2024-01-02 14:02:37

Daidzein Structure
Daidzein structure
 Common Name Daidzein
CAS Number 486-66-8 Molecular Weight 254.238
Density 1.4±0.1 g/cm3 Boiling Point 512.8±50.0 °C at 760 mmHg
Molecular Formula C15H10O4 Melting Point 315-323°C (dec.)
MSDS Chinese USA Flash Point 201.2±23.6 °C
Symbol GHS07
GHS07		 Signal Word Warning

 Use of Daidzein


Daidzein is a soy isoflavone, which acts as a PPAR activator.

 Names

Name daidzein
Synonym More Synonyms

 Daidzein Biological Activity

Description Daidzein is a soy isoflavone, which acts as a PPAR activator.
Related Catalog
Target

PPAR-α

PPAR-γ

In Vitro In 3T3-L1 adipocytes, Daidzein inverses the attenuation of adiponectin gene expression by co-culture, and these effects are inhibited by the PPAR-γ specific inhibitor. Daidzein attenuates the reduction of adiponectin expression in adipocytes, and a PPAR-γ specific inhibitor abrogated this effect. Direct activation of PPAR-α and-γ by Daidzein is confirmed by a luciferase reporter assay. In HEK293T cells, Daidzein significantly increases PPAR-α transcriptional activity in a concentration-dependent manner. Although an obvious dose-dependency is not observed in PPAR-γ transcriptional activity, Daidzein also significantly increases PPAR-γ transcriptional activity over a similar range of concentrations at which Daidzein enhanced PPAR-α transcriptional activity, with a maximum increase at 25 μM[1]. Daidzein is a soy isoflavone, which upregulates the expression of Abcg1, and it promotes axonal outgrowth in cultured hippocampal neurons via estrogen receptor signaling. Daidzein is a major component of soy with structural similarity to estrogen. It exerts an anti-inflammatory effect, lowers lipid levels, and increases mitochondrial biogenesis. As an activator of nuclear receptor peroxisome proliferator-activated receptors (PPARs), Daidzein enhances transcription of PPARs-dependent genes, including liver X receptors (LXRs, Nr1h gene family in mice). Incubation with different concentrations of Daidzein, from 5 to 100 μM, increases APOE transcriptional activity[2].
In Vivo Treating Apoe KO mice with Daidzein increases Lxr and Abca1 gene expression at 1 month after stroke, showing that the absence of ApoE does not interfere with other cholesterol homeostasis genetic programs. Therefore, the findings suggest that Daidzein-induced ApoE upregulation is a critical component in fostering functional recovery in chronic stroke[2].
Cell Assay HEK293T cells are plated on 24-well plates at a cell density of approximately 2.5×104 cells/well and are grown to 70-80% confluence. Cells are then transiently transfected with a PPAR-α or PPAR-γ expression plasmid, and a plasmid containing the luciferase gene under the control of three tandem PPAR response elements (PPRE × 3 TK-luciferase) using an X-treme GENE HP DNA Transfection Reagent. Renilla luciferase control vectors are co-transfected to control for transfection efficiency. After transfection, cells are cultured for another 24 h in medium containing DMSO or various concentrations (6.25, 12.5, 25 μM) of Daidzein. Cells are lysed, and luciferase activity is measured and expressed as fold induction, that is normalized to the activity of the renilla luciferase control plasmid[1].
Animal Admin Mice[2] Experiments are performed in 10- to 11-week-old male C57 (C57 bl/6) and Apoe KO (C57 background) mice. For long-term stroke recovery, mice receive Moxifloxacin (100 mg/kg) for 3 d. The prophylactic antibiotic treatment is shown to effectively reduce mortality in an animal model of stroke by attenuating peripheral infection. In addition, saline is subcutaneously administered daily, and hydrogel (Clear H2O) is given to prevent dehydration. With the implementation of poststroke care (antibiotic regimen, rehydration, and feeding hydrogels with soft diet) during the acute period (<1 week), mice start to regain their body weight by day 5 and continue to recover from stroke. Animals are randomly selected for vehicle or Daidzein treatment. Vehicle or Daidzein (10 mg/kg) is administered subcutaneously within 30 min of reperfusion after confirming the reperfusion of blood flow, daily for 7 d and then every other day up to 1 month.
References

[1]. Sakamoto Y1, et al. The Dietary Isoflavone Daidzein Reduces Expression of Pro-Inflammatory Genes through PPARα/γ and JNK Pathways in Adipocyte and Macrophage Co-Cultures. PLoS One. 2016 Feb 22;11(2):e0149676.

[2]. Kim E, et al. Daidzein Augments Cholesterol Homeostasis via ApoE to Promote Functional Recovery in Chronic Stroke. J Neurosci. 2015 Nov 11;35(45):15113-26.

 Chemical & Physical Properties

Density 1.4±0.1 g/cm3
Boiling Point 512.8±50.0 °C at 760 mmHg
Melting Point 315-323°C (dec.)
Molecular Formula C15H10O4
Molecular Weight 254.238
Flash Point 201.2±23.6 °C
Exact Mass 254.057907
PSA 70.67000
LogP 2.78
Vapour Pressure 0.0±1.4 mmHg at 25°C
Index of Refraction 1.699
Storage condition 2-8°C
Water Solubility insoluble

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
DJ3100040
CHEMICAL NAME :
4H-1-Benzopyran-4-one, 7-hydroxy-3-(4-hydroxyphenyl)-
CAS REGISTRY NUMBER :
486-66-8
BEILSTEIN REFERENCE NO. :
0231523
LAST UPDATED :
199709
DATA ITEMS CITED :
1
MOLECULAR FORMULA :
C15-H10-O4
MOLECULAR WEIGHT :
254.25

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
>2 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
PCJOAU Pharmaceutical Chemistry Journal (English Translation). Translation of KHFZAN. (Plenum Pub. Corp., 233 Spring St., New York, NY 10013) No.1- 1967- Volume(issue)/page/year: 13,51,1979

 Safety Information

Symbol GHS07
GHS07
Signal Word Warning
Hazard Statements H315-H319
Precautionary Statements P280-P305 + P351 + P338-P337 + P313
Personal Protective Equipment dust mask type N95 (US);Eyeshields;Gloves
Hazard Codes Xi:Irritant;
Risk Phrases R36/38
Safety Phrases S24-S26-S37/39
RIDADR NONH for all modes of transport
WGK Germany 3
RTECS DJ3100040

 Synthetic Route

 Articles157

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A novel UHPLC method for the rapid and simultaneous determination of daidzein, genistein and equol in human urine.

J. Chromatogr. B. Analyt. Technol. Biomed. Life Sci. 1005 , 1-8, (2015)

This work reports on a novel method involving reverse-phased ultra-high performance liquid chromatography (UHPLC) plus a spectrophotometric photodiode array/fluorescence (FLR) detection system for det...

 Synonyms

4H-1-Benzopyran-4-one, 7-hydroxy-3-(4-hydroxyphenyl)-
k251b
K 251-6
MFCD00016954
Tatoin
Soybean Extract
7-Hydroxy-3-(4-hydroxyphenyl)-4H-chromen-4-one
7-Hydroxy-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one (7-Hydroxy-3-(4-hydroxyphenyl)chromone
4',7-Dihydroxyisoflavone
Daidzeol
7-Hydroxy-3-(4-hydroxy phenyl) chromone
EINECS 207-635-4
7,4'-dihydroxyisoflavone
isoaurostatin
Daizeol
Daidzein
Daidsein
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