Dinosterol

Title: Dinosterol
CAS Registry Number: 58670-63-6
CAS Name: (3b,4a,5a,22E)-4,23-Dimethylergost-22-en-3-ol
Additional Names: 4a-methyl-5a(H)-D22-23,24-dimethylcholesten-3b-ol; Black Sea sterol
Molecular Formula: C30H52O
Molecular Weight: 428.73
Percent Composition: C 84.04%, H 12.23%, O 3.73%
Literature References: Biogenetically important marine sterol isolated from the toxic dinoflagellate, Gonyaulax tamarensis. Isoln and structure determn: Y. Shimizu et al., J. Am. Chem. Soc. 98, 1059 (1976). Stereochemistry: J. Finer et al., J. Org. Chem. 43, 1990 (1978). Identity with the Black Sea sterol: J. J. Boon et al., Nature 277, 125 (1979). Stereospecific synthesis: A. Y. L. Shu, C. Djerassi, Tetrahedron Lett. 22, 4627 (1981).
Properties: Needles from methanol-chloroform, mp 220-222° (Shimizu). Also reported as mp 211-214° (Shu, Djerassi). [a]20D -2.2° (in CHCl3).
Melting point: mp 220-222°; mp 211-214° (Shu, Djerassi)
Optical Rotation: [a]20D -2.2° (in CHCl3)
DINP Dinsed Diopterin Dioscin Dioscorea

Dinosterol
Dinosterol.svg
Identifiers
CAS number 58670-63-6 N
PubChem 6441076
ChemSpider 4945298 YesY
Jmol-3D images Image 1
Properties
Molecular formula C30H52O
Molar mass 428.73 g mol−1
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Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Dinosterol is a type of steroid produced by several genera of dinoflagellates. It is a 4α-methyl sterol (4α,23,24-trimethyl-5α-cholest-22E-en-3β-ol) rarely found in other classes of protists.[1]

This sterol and others have been considered as class-specific, being biomarkers for dinoflagellates, although dinosterol is produced in minor amounts by a small number of other phytoplankton, such as the marine diatom Navicula speciosa.[2] and Prymnesiophytes of the genus Pavlova.[3]

Dinosterols show similar abundances as dinocysts.[4] Other studies found a nonlinear [5] or did not find a direct link between dinocyst abundances and sterol concentrations.[6]

Dinosterol has been used as indicator for dinoflagellate production in the Cariaco Basin.[7][8]

Hydrogen isotope ratios in dinosterols can serve to reconstruct salinity semi-quantitatively.[9]

Some studies have shown that certain dinoflagellates produce sterols that have the potential to serve as genera-specific biomarkers.[10][11] Recent work showed that dinoflagellate genera, which formed discrete clusters in the 18S rDNA-based phylogeny, shared similar sterol compositions. This suggested that the sterol compositions of dinoflagellates are explained by the evolutionary history of this lineage.[12]