Spiculisporic acid | CAS#469-77-2

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

MedKoo CAT#: 462976

CAS#: 469-77-2

Description: Spiculisporic acid is a biosurfactant that has been found in P. spiculisporum.

Chemical Structure

Spiculisporic acid

CAS# 469-77-2

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 462976
Name: Spiculisporic acid
CAS#: 469-77-2
Chemical Formula: C17H28O6
Exact Mass: 328.19
Molecular Weight: 328.410
Elemental Analysis: C, 62.18; H, 8.59; O, 29.23

Price and Availability

Size	Price	Availability
1g	USD 200	2 Weeks
5mg	USD 350	2 Weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Synonym: (–)-Spiculisporic Acid; NSC 244387; NSC244387; NSC-244387;

IUPAC/Chemical Name: (S)-2-((S)-1-carboxyundecyl)-5-oxotetrahydrofuran-2-carboxylic acid

InChi Key: TUXHHVJPGQUPCF-DYVFJYSZSA-N

InChi Code: InChI=1S/C17H28O6/c1-2-3-4-5-6-7-8-9-10-13(15(19)20)17(16(21)22)12-11-14(18)23-17/h13H,2-12H2,1H3,(H,19,20)(H,21,22)/t13-,17+/m1/s1

SMILES Code: CCCCCCCCCC[C@H](C(O)=O)[C@]1(OC(CC1)=O)C(O)=O

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, DMF, and ethanol

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:	Spiculisporic acid is a biosurfactant.
In vitro activity:	The crystal of spiculisporic acid is orthorhombic, and the space group is P2₁ 2₁ 2₁ with Z = 4 at 23°C. Sodium salts of the lactone-cleaved derivative of spiculisporic acid (O-acid), showed large dispersing and calcium ion sequestration properties due to their plural polar heads. Reference: J Oleo Sci. 2013;62(10):795-802. https://pubmed.ncbi.nlm.nih.gov/24088517/
In vivo activity:	To be determined

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMF	30.0	91.35
	DMSO	30.0	91.35
	Ethanol	30.0	91.35

Preparing Stock Solutions

The following data is based on the product molecular weight 328.41 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. Osama S, El Sherei M, Al-Mahdy DA, Bishr M, Salama O, Raafat MM. Antimicrobial activity of spiculisporic acid isolated from endophytic fungus Aspergillus cejpii of Hedera helix against MRSA. Braz J Microbiol. 2024 Jan 17. doi: 10.1007/s42770-023-01224-7. Epub ahead of print. PMID: 38231376. 2. Ishigami Y, Zhang Y, Goto M. Molecular and crystal structure of spiculisporic acid and correlation with the surface activity. J Oleo Sci. 2013;62(10):795-802. doi: 10.5650/jos.62.795. PMID: 24088517.
In vitro protocol:	1. Osama S, El Sherei M, Al-Mahdy DA, Bishr M, Salama O, Raafat MM. Antimicrobial activity of spiculisporic acid isolated from endophytic fungus Aspergillus cejpii of Hedera helix against MRSA. Braz J Microbiol. 2024 Jan 17. doi: 10.1007/s42770-023-01224-7. Epub ahead of print. PMID: 38231376. 2. Ishigami Y, Zhang Y, Goto M. Molecular and crystal structure of spiculisporic acid and correlation with the surface activity. J Oleo Sci. 2013;62(10):795-802. doi: 10.5650/jos.62.795. PMID: 24088517.
In vivo protocol:	To be determined

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*When preparing stock solutions always use the batch-specific molecular weight of the product found on the vial label and SDS / CoA (available online).

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1: Guo Z, Gai C, Cai C, Chen L, Liu S, Zeng Y, Yuan J, Mei W, Dai H. Metabolites with Insecticidal Activity from Aspergillus fumigatus JRJ111048 Isolated from Mangrove Plant Acrostichum specioum Endemic to Hainan Island. Mar Drugs. 2017 Dec 6;15(12):381. doi: 10.3390/md15120381. PMID: 29211003; PMCID: PMC5742841.

2: Wang R, Guo ZK, Li XM, Chen FX, Zhan XF, Shen MH. Spiculisporic acid analogues of the marine-derived fungus, Aspergillus candidus strain HDf2, and their antibacterial activity. Antonie Van Leeuwenhoek. 2015 Jul;108(1):215-9. doi: 10.1007/s10482-015-0462-y. Epub 2015 Apr 26. PMID: 25912731.

3: Kuml D, Dethoup T, Buttachon S, Singburaudom N, Silva AM, Kijjoa A. Spiculisporic acid E, a new spiculisporic acid derivative and ergosterol derivatives from the marine-sponge associated fungus Talaromyces trachyspermus (KUFA 0021). Nat Prod Commun. 2014 Aug;9(8):1147-50. PMID: 25233594.

4: Ishigami Y, Zhang Y, Goto M. Molecular and crystal structure of spiculisporic acid and correlation with the surface activity. J Oleo Sci. 2013;62(10):795-802. doi: 10.5650/jos.62.795. PMID: 24088517.

5: Yilmaz N, Houbraken J, Hoekstra ES, Frisvad JC, Visagie CM, Samson RA. Delimitation and characterisation of Talaromyces purpurogenus and related species. Persoonia. 2012 Dec;29:39-54. doi: 10.3767/003158512X659500. Epub 2012 Nov 12. PMID: 23606764; PMCID: PMC3589794.

6: Wang R, Liu TM, Shen MH, Yang MQ, Feng QY, Tang XM, Li XM. Spiculisporic acids B–D, three new γ-butenolide derivatives from a sea urchin-derived fungus Aspergillus sp. HDf2. Molecules. 2012 Nov 5;17(11):13175-82. doi: 10.3390/molecules171113175. PMID: 23128094; PMCID: PMC6268229.

7: Brown SP, Goodwin NC, MacMillan DW. The first enantioselective organocatalytic Mukaiyama-Michael reaction: a direct method for the synthesis of enantioenriched gamma-butenolide architecture. J Am Chem Soc. 2003 Feb 5;125(5):1192-4. doi: 10.1021/ja029095q. PMID: 12553821.

8: Frisvad JC, Filtenborg O, Samson RA, Stolk AC. Chemotaxonomy of the genus Talaromyces. Antonie Van Leeuwenhoek. 1990 Apr;57(3):179-89. doi: 10.1007/BF00403953. PMID: 2181929.

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