Spirolaxine | CAS#126382-01-2

MedKoo Cat#: 329678 | Name: Spirolaxine

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Description:

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

Spirolaxine is a natural product isolated from Sporotrichum laxum ATCC 15155, which has shown a variety of biological activities including promising anti-Helicobacter pylori property.

Chemical Structure

Spirolaxine

CAS#126382-01-2

Theoretical Analysis

MedKoo Cat#: 329678

Name: Spirolaxine

CAS#: 126382-01-2

Chemical Formula: C23H32O6

Exact Mass: 404.2199

Molecular Weight: 404.50

Elemental Analysis: C, 68.29; H, 7.97; O, 23.73

Price and Availability

Size	Price	Availability	Quantity
2mg	USD 1,250.00

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Related CAS #

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Synonym

Spirolaxine

IUPAC/Chemical Name

5-hydroxy-7-methoxy-3R-[5-[(2R,5R,7R)-2-methyl-1,6-dioxaspiro[4.5]dec-7-yl]pentyl]-1(3H)-isobenzofuranone

InChi Key

CZIMFHQXGMXDMO-DGROVODQSA-N

InChi Code

InChI=1S/C23H32O6/c1-15-10-12-23(28-15)11-6-8-17(29-23)7-4-3-5-9-19-18-13-16(24)14-20(26-2)21(18)22(25)27-19/h13-15,17,19,24H,3-12H2,1-2H3/t15-,17-,19-,23-/m1/s1

SMILES Code

O=C1O[C@H](CCCCC[C@H](CCC2)O[C@]32CC[C@@H](C)O3)C4=C1C(OC)=CC(O)=C4

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

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:

Spirolaxine is a potent anti-H. pylori agent (MIC = 0.2 µg/cm3) with weak activity against E. coli.

In vitro activity:

To be determined

In vivo activity:

To be determined

Preparing Stock Solutions

The following data is based on the product molecular weight 404.50 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:

To be determined

In vitro protocol:

To be determined

In vivo protocol:

To be determined

1: Sun L, Wang S, Zhang S, Yu D, Qin Y, Huang H, Wang W, Zhan J. Identification of a type III polyketide synthase involved in the biosynthesis of spirolaxine. Appl Microbiol Biotechnol. 2016 Aug;100(16):7103-13. doi: 10.1007/s00253-016-7444-5. Epub 2016 Mar 29. PubMed PMID: 27023915. 2: Wang S, Zhang S, Zhou T, Zhan J. Three new resorcylic acid derivatives from Sporotrichum laxum. Bioorg Med Chem Lett. 2013 Nov 1;23(21):5806-9. doi: 10.1016/j.bmcl.2013.08.109. Epub 2013 Sep 7. PubMed PMID: 24070784; PubMed Central PMCID: PMC3825103. 3: Yadav JS, Sreenivas M, Srinivas Reddy A, Subba Reddy BV. A practical total synthesis of (+)-spirolaxine methyl ether. J Org Chem. 2010 Dec 3;75(23):8307-10. doi: 10.1021/jo1016647. Epub 2010 Nov 8. PubMed PMID: 21058660. 4: Sperry J, Liu YC, Brimble MA. Synthesis of natural products containing spiroketals via intramolecular hydrogen abstraction. Org Biomol Chem. 2010 Jan 7;8(1):29-38. doi: 10.1039/b916041h. Epub 2009 Oct 7. PubMed PMID: 20024126. 5: Radcliff FJ, Fraser JD, Wilson ZE, Heapy AM, Robinson JE, Bryant CJ, Flowers CL, Brimble MA. Anti-Helicobacter pylori activity of derivatives of the phthalide-containing antibacterial agents spirolaxine methyl ether, CJ-12,954, CJ-13,013, CJ-13,102, CJ-13,104, CJ-13,108 and CJ-13,015. Bioorg Med Chem. 2008 Jun 1;16(11):6179-85. doi: 10.1016/j.bmc.2008.04.037. Epub 2008 Apr 18. PubMed PMID: 18457954. 6: Nasini G, Bava A, Fronza G, Giannini G. Microbial transformation of spirolaxine, a bioactive undecaketide fungal metabolite from the basidiomycete Sporotrichum laxum. Chem Biodivers. 2007 Dec;4(12):2772-9. PubMed PMID: 18081087. 7: Robinson JE, Brimble MA. Synthesis of the anti-Helicobacter pylori agent (+)-spirolaxine methyl ether and the unnatural (2"S)-diastereomer. Org Biomol Chem. 2007 Aug 21;5(16):2572-82. PubMed PMID: 18019531. 8: Trost BM, Weiss AH. An alkyne strategy for the asymmetric synthesis of natural products: application to (+)-spirolaxine methyl ether. Angew Chem Int Ed Engl. 2007;46(40):7664-6. PubMed PMID: 17722127. 9: Keaton KA, Phillips AJ. A cyclopropanol-based strategy for subunit coupling: total synthesis of (+)-spirolaxine methyl ether. Org Lett. 2007 Jul 5;9(14):2717-9. Epub 2007 Jun 9. PubMed PMID: 17559220. 10: Nannei R, Dallavalle S, Merlini L, Bava A, Nasini G. Synthesis of (+)-spirolaxine methyl ether. J Org Chem. 2006 Aug 4;71(16):6277-80. PubMed PMID: 16872220. 11: Robinson JE, Brimble MA. The first enantioselective total synthesis of the anti-Helicobacter pylori agent (+)-spirolaxine methyl ether. Chem Commun (Camb). 2005 Mar 28;(12):1560-2. Epub 2005 Jan 26. PubMed PMID: 15770259.