Spiculisporic acid | CAS#469-77-2 | Biosurfactant

MedKoo Cat#: 462976 | Name: Spiculisporic acid

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Description:

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

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

Chemical Structure

Spiculisporic acid

CAS#469-77-2

Theoretical Analysis

MedKoo Cat#: 462976

Name: Spiculisporic acid

CAS#: 469-77-2

Chemical Formula: C17H28O6

Exact Mass: 328.1886

Molecular Weight: 328.41

Elemental Analysis: C, 62.18; H, 8.59; O, 29.23

Price and Availability

Size	Price	Availability	Quantity
1g	USD 200.00	2 Weeks
5mg	USD 350.00	2 Weeks

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Related CAS #

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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

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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

	Solvent	mg/mL	mM
Solubility
	DMF	30.0	91.35
	DMSO	30.0	91.35
	Ethanol	30.0	91.35

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 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:

In vivo protocol:

To be determined

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 Mar;55(1):515-527. doi: 10.1007/s42770-023-01224-7. Epub 2024 Jan 17. PMID: 38231376; PMCID: PMC10920557. 2: Wang Y, Sun Y, Wang Y, Jia S, Qiao Y, Zhou Z, Shao W, Zhang X, Guo J, Song X, Niu X, Peng D. Urine metabolomics phenotyping and urinary biomarker exploratory in mild cognitive impairment and Alzheimer's disease. Front Aging Neurosci. 2023 Dec 22;15:1273807. doi: 10.3389/fnagi.2023.1273807. PMID: 38187356; PMCID: PMC10768723. 3: Sharma M, Bharti S, Goswami A, Mallubhotla S. Diversity, Antimicrobial, Antioxidant, and Anticancer Activity of Culturable Fungal Endophyte Communities in Cordia dichotoma. Molecules. 2023 Oct 4;28(19):6926. doi: 10.3390/molecules28196926. PMID: 37836769; PMCID: PMC10574381. 4: Coulibaly AE, Pakora GA, Ako ABA, Amari GELD, N'Guessan CA, Kouabenan A, Kone D, Djaman JA. Diversity of Sclerotium rolfsii antagonist fungi isolated from soils of the rhizosphere of tomato crops and identification of some antifungal compounds. Heliyon. 2022 Feb 11;8(2):e08943. doi: 10.1016/j.heliyon.2022.e08943. PMID: 35243065; PMCID: PMC8857420. 5: Moriwaki-Takano M, Asada C, Nakamura Y. Production of spiculisporic acid by Talaromyces trachyspermus in fed-batch bioreactor culture. Bioresour Bioprocess. 2021 Jul 10;8(1):59. doi: 10.1186/s40643-021-00414-1. PMID: 38650186; PMCID: PMC10991155. 6: 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. 7: 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. 8: 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. 9: 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. 10: 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. 11: 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. 12: 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. 13: 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.