Sophoricoside | CAS#152-95-4 | Diverse isoflavone glycoside

MedKoo Cat#: 464987 | Name: Sophoricoside

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Description:

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

Sophoricoside is a polyketide synthase-derived isoflavone glycoside that has been found in S. japonica and has diverse biological activities. It inhibits lipid accumulation induced by oleic acid in HepG2 cells and stimulates glucose uptake in C2C12 mouse skeletal muscle myoblasts when used at a concentration of 10 µM. Sophoricoside (2 mg/kg) reduces scratching behavior induced by compound 48/80 or histamine in mice, as well as reduces serum levels of IgE in a mouse model of atopic dermatitis. It increases serum levels of osteocalcin and alkaline phosphatase (ALP) and restores mechanical bone hardness in an ovariectomized rat model of osteoporosis. Sophoricoside (80 and 160 mg/kg) decreases hepatic cholesterol and triglyceride levels, serum LDL and apolipoprotein B levels, and hepatic injury in a mouse model of fructose-induced liver injury.

Chemical Structure

Sophoricoside

CAS#152-95-4

Theoretical Analysis

MedKoo Cat#: 464987

Name: Sophoricoside

CAS#: 152-95-4

Chemical Formula: C21H20O10

Exact Mass: 432.1056

Molecular Weight: 432.38

Elemental Analysis: C, 58.34; H, 4.66; O, 37.00

Price and Availability

Size	Price	Availability
50mg	USD 300.00	2 Weeks
100mg	USD 450.00	2 Weeks
250mg	USD 750.00	2 Weeks
500mg	USD 1,250.00	2 Weeks

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Related CAS #

No Data

Synonym

Sophoricoside; Genistein 4′-O-glucoside;

IUPAC/Chemical Name

5,7-dihydroxy-3-(4-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)phenyl)-4H-chromen-4-one

InChi Key

ISQRJFLLIDGZEP-CMWLGVBASA-N

InChi Code

InChI=1S/C21H20O10/c22-7-15-18(26)19(27)20(28)21(31-15)30-11-3-1-9(2-4-11)12-8-29-14-6-10(23)5-13(24)16(14)17(12)25/h1-6,8,15,18-24,26-28H,7H2/t15-,18-,19+,20-,21-/m1/s1

SMILES Code

OC1=CC(O)=C2C(OC=C(C2=O)C3=CC=C(C=C3)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)=C1

Appearance

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

To be determined

Shelf Life

>2 years if stored properly

Drug Formulation

To be determined

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

Instruction

View handling instruction

	Solvent	mg/mL	mM
Solubility
	DMF	25.0	57.82
	DMSO	25.0	57.82
	DMSO:PBS (pH 7.2) (1:2)	0.3	0.69

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 432.38 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

1: GABOR M. [The hormonal effect of an isoflavone derivative (sophoricoside)]. Kiserl Orvostud. 1961 May;13:133-4. Hungarian. PMID: 13702797. 2: Fraga CG, Martino VS, Ferraro GE, Coussio JD, Boveris A. Flavonoids as antioxidants evaluated by in vitro and in situ liver chemiluminescence. Biochem Pharmacol. 1987 Mar 1;36(5):717-20. doi: 10.1016/0006-2952(87)90724-6. PMID: 3827953. 3: Liu IM, Sheu SJ. Analysis and processing of Chinese herbal drugs. VIII: The study of sophorae floe. Am J Chin Med. 1989;17(3-4):179-87. doi: 10.1142/S0192415X89000279. PMID: 2633619. 4: Gábor M, Rázga Z. Effect of benzopyrone derivatives on simultaneously induced croton oil ear oedema and carrageenin paw oedema in rats. Acta Physiol Hung. 1991;77(3-4):197-207. PMID: 1755324. 5: Min B, Oh SR, Lee HK, Takatsu K, Chang IM, Min KR, Kim Y. Sophoricoside analogs as the IL-5 inhibitors from Sophora japonica. Planta Med. 1999 Jun;65(5):408-12. doi: 10.1055/s-1999-14016. PMID: 10418325. 6: Yun J, Lee CK, Chang IM, Takatsu K, Hirano T, Min KR, Lee MK, Kim Y. Differential inhibitory effects of sophoricoside analogs on bioactivity of several cytokines. Life Sci. 2000 Oct 27;67(23):2855-63. doi: 10.1016/s0024-3205(00)00873-0. PMID: 11106000. 7: Yun J, Oh SR, Lee HK, Chang IM, Takatsu K, Yun YP, Min KR, Kim Y. Effect of genistein analogs on oxygen radical production in leukocytes stimulated by unopsonized zymosan. Planta Med. 2001 Apr;67(3):274-6. doi: 10.1055/s-2001-12002. PMID: 11345702. 8: Kim BH, Chung EY, Ryu JC, Jung SH, Min KR, Kim Y. Anti-inflammatory mode of isoflavone glycoside sophoricoside by inhibition of interleukin-6 and cyclooxygenase-2 in inflammatory response. Arch Pharm Res. 2003 Apr;26(4):306-11. doi: 10.1007/BF02976960. PMID: 12735689. 9: Jung SH, Cho SH, Dang TH, Lee JH, Ju JH, Kim MK, Lee SH, Ryu JC, Kim Y. Structural requirement of isoflavonones for the inhibitory activity of interleukin-5. Eur J Med Chem. 2003 May;38(5):537-45. doi: 10.1016/s0223-5234(03)00064-3. PMID: 12767605. 10: Kim BH, Chung EY, Min BK, Lee SH, Kim MK, Min KR, Kim Y. Anti-inflammatory action of legume isoflavonoid sophoricoside through inhibition on cyclooxygenase-2 activity. Planta Med. 2003 May;69(5):474-6. doi: 10.1055/s-2003-39712. PMID: 12802736. 11: Du N, Xu Y, Chen WZ, Zhang FH. [Effect of Sophoricoside on histomorphology of bone in ovariectomized rats]. Zhong Xi Yi Jie He Xue Bao. 2003 May;1(1):44-6. Chinese. doi: 10.3736/jcim20030118. PMID: 15339615. 12: Yang HM, Shin HR, Cho SH, Bang SC, Song GY, Ju JH, Kim MK, Lee SH, Ryu JC, Kim Y, Jung SH. Structural requirement of chalcones for the inhibitory activity of interleukin-5. Bioorg Med Chem. 2007 Jan 1;15(1):104-11. doi: 10.1016/j.bmc.2006.10.007. Epub 2006 Oct 10. PMID: 17064909. 13: Yang HM, Shin HR, Cho SH, Song GY, Lee IJ, Kim MK, Lee SH, Ryu JC, Kim Y, Jung SH. The role of the hydrophobic group on ring A of chalcones in the inhibition of interleukin-5. Arch Pharm Res. 2006 Nov;29(11):969-76. doi: 10.1007/BF02969280. PMID: 17146965. 14: Wang W, Tang J, Wang S, Zhou L, Hu Z. Method development for the determination of coumarin compounds by capillary electrophoresis with indirect laser-induced fluorescence detection. J Chromatogr A. 2007 Apr 27;1148(1):108-14. doi: 10.1016/j.chroma.2006.09.070. Epub 2007 Mar 26. PMID: 17383667. 15: Yang HM, Shin HR, Bang SC, Lee KC, Hoang le TA, Lee IJ, Kim Y, Jung SH. The role of alkoxy group on the A ring of isoflavones in the inhibition of interleukin-5. Arch Pharm Res. 2007 Aug;30(8):950-4. doi: 10.1007/BF02993962. PMID: 17879747. 16: Xu Y, Chen WZ, Du N. [Effects of sophoricoside and genistein on biological characteristics of osteoblasts]. Zhong Xi Yi Jie He Xue Bao. 2009 Mar;7(3):223-7. Chinese. doi: 10.3736/jcim20090305. PMID: 19284950. 17: Luo R, Li Z, Qian G, Lu J, Fu C. Determination of sophoricoside in rat plasma by HPLC and its application to pharmacokinetic studies. Yakugaku Zasshi. 2009 Dec;129(12):1545-9. doi: 10.1248/yakushi.129.1545. PMID: 19952535. 18: El-Halawany AM, Chung MH, Abdallah HM, Nishihara T, Hattori M. Estrogenic activity of a naringinase-treated extract of Sophora japonica cultivated in Egypt. Pharm Biol. 2010 Feb;48(2):177-81. doi: 10.3109/13880200903062663. PMID: 20645836. 19: Yang R, Zeng HJ, Wang QW, Guo C, Li JJ, Qu LB. Simultaneous determination of eight active components in Chinese medicine 'JiangYaBiFeng' tablet by HPLC coupled with diode array detection. J Pharm Biomed Anal. 2011 Jun 1;55(3):552-6. doi: 10.1016/j.jpba.2011.01.021. Epub 2011 Jan 22. PMID: 21376498. 20: Zeng HJ, Yang R, Guo C, Wang QW, Qu LB, Li JJ. Pharmacokinetic study of six flavones in rat plasma and tissues after oral administration of 'JiangYaBiFeng' using SPE-HPLC-DAD. J Pharm Biomed Anal. 2011 Dec 5;56(4):815-9. doi: 10.1016/j.jpba.2011.07.015. Epub 2011 Jul 22. PMID: 21831556.