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Molecular and Crystal Structure of Spiculisporic Acid and Correlation With the Surface Activity

Molecular and Crystal Structure of Spiculisporic Acid and Correlation With the Surface Activity

Yutaka Ishigami, Yuejun Zhang, Midori Goto

J Oleo Sci. 2013;62(10):795-802.

PMID: 24088517

Abstract:

The crystal of spiculisporic acid, [4S, 5S-(4,5-dicarboxy-4-pentadecanolide)], is orthorhombic, and the space group is P2₁ 2₁ 2₁ with Z = 4 at 23°C. The cell dimensions are as follows, a = 43.82 (1) Å, b = 7.540 (2) Å, c = 5.579 (2) Å, V = 1843 (1) Å³. The molecules form intermolecular networks linked by hydrogen bonds around their polar carboxylic moieties. The hydrophobicity of the lactone ring (γ-butanolide) was evaluated at ca. 4 methylene linkages of n-alkyl chain from both of the molecular alignmental data and the surface active properties of sodium spiculisporates. Then, it was made clear that sodium spiculisporates, anionic polyfunctional biosurfactants, exerted a distinctive characteristic of lower critical micelle concentration (cmc) and γ(cmc) (surface tension at the cmc), simultaneously, through their properties. On the other hand, 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.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP106025	Pentadecanolide		106-02-5	Price

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