Dihydrogenistein | CAS# 21554-71-2 | Biochemical

MedKoo Cat#: 574668 | Name: Dihydrogenistein

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Dihydrogenistein is a derivative of Genistein -- a compound that exhibits specific inhibitory activity against tyrosine kinases including autophosphorylation of epidermal growth factor receptor kinase.

Chemical Structure

Dihydrogenistein

CAS#21554-71-2

Theoretical Analysis

MedKoo Cat#: 574668

Name: Dihydrogenistein

CAS#: 21554-71-2

Chemical Formula: C15H12O5

Exact Mass: 272.0685

Molecular Weight: 272.26

Elemental Analysis: C, 66.17; H, 4.44; O, 29.38

Price and Availability

Size	Price	Availability	Quantity
25mg	USD 450.00	2 Weeks

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Synonym

Dihydrogenistein; 5,7,4'-trihydroxyisoflavanone; 4',5,7-trihydroxyisoflavanone

IUPAC/Chemical Name

2,3-Dihydro-5,7-dihydroxy-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one

InChi Key

UQGVUYNHDKMLSE-UHFFFAOYSA-N

InChi Code

InChI=1S/C15H12O5/c16-9-3-1-8(2-4-9)11-7-20-13-6-10(17)5-12(18)14(13)15(11)19/h1-6,11,16-18H,7H2

SMILES Code

O=C1C(C2=CC=C(O)C=C2)COC3=CC(O)=CC(O)=C13

Appearance

Beige solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>3 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Dihydrogenistein is a derivative of Genistein.

In vitro activity:

Although not exhibiting any visible toxicity on the HEK-cGASlow cells at the doses used, Genistein treatment reduced cell proliferation above 30 μM (Fig. S1A). To circumvent this, this study normalized the number of cGAMP-producing cells after Genistein treatment and confirmed a dose-dependent inhibition of cGAMP transactivation of cocultured LL171 cells by Genistein (Fig. 1C). Similarly, pretreatment of connexin (CX) expressing human MG-63 cells with Genistein, that were subsequently transfected with an immunostimulatory DNA (ISD) to activate cGAS, significantly decreased ISRE-luciferase expression from cocultured LL171 cells (Fig. 1D). It is noteworthy that intracellular levels of cGAMP were increased by Genistein in HEK cGASlow cells (Fig. 1E), indicating an inhibition of GJIC aligned with the accumulating cGAMP levels observed. Reference: mBio. 2022 Aug 30;13(4):e0206422. https://pubmed.ncbi.nlm.nih.gov/35924852/

In vivo activity:

The mfn2 expression and mitochondrial membrane potential in DN group were significantly higher than those in control group, which were also increased in each treatment group with genistein in a dose-dependent manner (Figs. 3a and 3b). It shows that genistein supplementation improves nephropathy likely via modulation of the mitochondrial fusion and function in DN rats. Reference: Acta Cir Bras. 2022 Aug 15;37(6):e370601. https://pubmed.ncbi.nlm.nih.gov/35976278/

Preparing Stock Solutions

The following data is based on the product molecular weight 272.26 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Ullah TR, Balka KR, Ambrose RL, Pépin G, Wilce MCJ, Wilce JA, Thomas BJ, De Nardo D, Williams BRG, Gantier MP. Genistein Targets STING-Driven Antiviral Responses. mBio. 2022 Aug 30;13(4):e0206422. doi: 10.1128/mbio.02064-22. Epub 2022 Aug 4. PMID: 35924852; PMCID: PMC9426420. 2. Cong L, Xie X, Liu S, Xiang L, Fu X. Genistein promotes M1 macrophage apoptosis and reduces inflammatory response by disrupting miR-21/TIPE2 pathway. Saudi Pharm J. 2022 Jul;30(7):934-945. doi: 10.1016/j.jsps.2022.05.009. Epub 2022 May 23. PMID: 35903524; PMCID: PMC9315303. 3. Li Y, Ou S, Liu Q, Gan L, Zhang L, Wang Y, Qin J, Liu J, Wu W. Genistein improves mitochondrial function and inflammatory in rats with diabetic nephropathy via inhibiting MAPK/NF-κB pathway. Acta Cir Bras. 2022 Aug 15;37(6):e370601. doi: 10.1590/acb370601. PMID: 35976278; PMCID: PMC9377651. 4. Siriviriyakul P, Sriko J, Somanawat K, Chayanupatkul M, Klaikeaw N, Werawatganon D. Genistein attenuated oxidative stress, inflammation, and apoptosis in L-arginine induced acute pancreatitis in mice. BMC Complement Med Ther. 2022 Aug 4;22(1):208. doi: 10.1186/s12906-022-03689-9. PMID: 35927726; PMCID: PMC9351145.

In vitro protocol:

In vivo protocol:

1. Li Y, Ou S, Liu Q, Gan L, Zhang L, Wang Y, Qin J, Liu J, Wu W. Genistein improves mitochondrial function and inflammatory in rats with diabetic nephropathy via inhibiting MAPK/NF-κB pathway. Acta Cir Bras. 2022 Aug 15;37(6):e370601. doi: 10.1590/acb370601. PMID: 35976278; PMCID: PMC9377651. 2. Siriviriyakul P, Sriko J, Somanawat K, Chayanupatkul M, Klaikeaw N, Werawatganon D. Genistein attenuated oxidative stress, inflammation, and apoptosis in L-arginine induced acute pancreatitis in mice. BMC Complement Med Ther. 2022 Aug 4;22(1):208. doi: 10.1186/s12906-022-03689-9. PMID: 35927726; PMCID: PMC9351145.

1. Kobayashi S, Shinohara M, Nagai T, Konishi Y. Transport mechanisms for soy isoflavones and microbial metabolites dihydrogenistein and dihydrodaidzein across monolayers and membranes. Biosci Biotechnol Biochem. 2013;77(11):2210-2217. doi:10.1271/bbb.130404