Laxogenin

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

MedKoo CAT#: 598487

CAS#: 1177-71-5

Description: Laxogenin is a new steroidal sapogenin isolated from Smilax sieboldi Miq.

Chemical Structure

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Laxogenin
CAS# 1177-71-5
Instruction

Theoretical Analysis

MedKoo Cat#: 598487
Name: Laxogenin
CAS#: 1177-71-5
Chemical Formula: C27H42O4
Exact Mass: 430.31
Molecular Weight: 430.620
Elemental Analysis: C, 75.31; H, 9.83; O, 14.86

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

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Synonym: Laxogenin; 6-Oxotigogenin;

IUPAC/Chemical Name: (2aS,4S,5'R,6aR,6bS,8aS,8bR,9S,10R,11aS,12aS,12bR)-4-hydroxy-5',6a,8a,9-tetramethylicosahydrospiro[naphtho[2',1':4,5]indeno[2,1-b]furan-10,2'-pyran]-2(1H)-one

InChi Key: WOJKRRDDERNLBU-BOYSPROGSA-N

InChi Code: InChI=1S/C27H42O4/c1-15-5-10-27(30-14-15)16(2)24-23(31-27)13-20-18-12-22(29)21-11-17(28)6-8-25(21,3)19(18)7-9-26(20,24)4/h15-21,23-24,28H,5-14H2,1-4H3/t15-,16+,17+,18-,19+,20+,21-,23+,24+,25-,26+,27-/m1/s1

SMILES Code: C[C@@H]1CC[C@]2(OC1)[C@@H](C)[C@H]3[C@H](C[C@@H]4[C@]3(C)CC[C@H]5[C@H]4CC([C@@H]6[C@]5(C)CC[C@H](O)C6)=O)O2

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: 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: 2934.99.03.00

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 430.62 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.

Recalculate based on batch purity %
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:
In vitro protocol:
In vivo protocol:

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1: Wang Q, Xu J, Liu X, Gong W, Zhang C. Synthesis of brassinosteroids analogues from laxogenin and their plant growth promotion. Nat Prod Res. 2015;29(2):149-57. doi: 10.1080/14786419.2014.968151. Epub 2014 Oct 14. PubMed PMID: 25311045.

2: AKAHORI A, YASUDA F. [Laxogenin, a new steroidal sapogenin isolated from Smilax sieboldi Miq]. Yakugaku Zasshi. 1963 May;83:557-8. Japanese. PubMed PMID: 14041495.

3: Baba M, Ohmura M, Kishi N, Okada Y, Shibata S, Peng J, Yao SS, Nishino H, Okuyama T. Saponins isolated from Allium chinense G. Don and antitumor-promoting activities of isoliquiritigenin and laxogenin from the same drug. Biol Pharm Bull. 2000 May;23(5):660-2. PubMed PMID: 10823685.

4: Okanishi T, Akahori A, Yasuda F. Studies on the steroidal components of domestic plants. XLVII. Constituents of the stem of Smilax sieboldi Miq. (1). The structure of laxogenin. Chem Pharm Bull (Tokyo). 1965 May;13(5):545-50. PubMed PMID: 5867711.

5: Kubo S, Mimaki Y, Sashida Y, Nikaido T, Ohmoto T. Steroidal saponins from the rhizomes of Smilax sieboldii. Phytochemistry. 1992 Jul;31(7):2445-50. PubMed PMID: 1369386.

6: Yu B, Tao H. Glycosyl trifluoroacetimidates. 2. Synthesis of dioscin and xiebai saponin I. J Org Chem. 2002 Dec 13;67(25):9099-102. PubMed PMID: 12467439.

7: Timité G, Mitaine-Offer AC, Miyamoto T, Tanaka C, Mirjolet JF, Duchamp O, Lacaille-Dubois MA. Structure and cytotoxicity of steroidal glycosides from Allium schoenoprasum. Phytochemistry. 2013 Apr;88:61-6. doi: 10.1016/j.phytochem.2012.12.001. Epub 2013 Jan 25. PubMed PMID: 23357597.

8: Zhang YW, Morita I, Zhang L, Shao G, Yao XS, Murota S. Screening of anti-hypoxia/reoxygenation agents by an in vitro method. Part 2: Inhibition of tyrosine kinase activation prevented hypoxia/reoxygenation-induced injury in endothelial gap junctional intercellular communication. Planta Med. 2000 Mar;66(2):119-23. PubMed PMID: 10763583.

9: Zhang YW, Morita I, Shao G, Yao XS, Murota S. Screening of anti-hypoxia/reoxygenation agents by an in vitro model. Part 1: Natural inhibitors for protein tyrosine kinase activated by hypoxia/reoxygenation in cultured human umbilical vein endothelial cells. Planta Med. 2000 Mar;66(2):114-8. PubMed PMID: 10763582.

10: Pérez-Labrada K, Brouard I, Estévez S, Marrero MT, Estévez F, Bermejo J, Rivera DG. New insights into the structure-cytotoxicity relationship of spirostan saponins and related glycosides. Bioorg Med Chem. 2012 Apr 15;20(8):2690-700. doi: 10.1016/j.bmc.2012.02.026. Epub 2012 Feb 15. PubMed PMID: 22405922.