dinosterol

Dinosterol (4α,23,24-trimethyl-5α-cholest-22E-en-3β-ol) is a 4α-methyl sterol that is produced by several genera of dinoflagellates and is rarely found in other classes of protists. The steroidal alkane, dinosterane, is the 'molecular fossil' of dinosterol, meaning that dinosterane has the same carbon skeleton as dinosterol, but lacks dinosterol's hydroxyl group and olefin functionality. As such, dinosterane is often used as a biomarker to identify the presence of dinoflagellates in sediments.

Chemical data

Formula: C30H52O
Molecular weight: 428.7 g/mol
IUPAC name: (3S,4S,5S,8S,9S,10R,13R,14S,17R)-4,10,13-trimethyl-17-[(E,2R,5R)-4,5,6-trimethylhept-3-en-2-yl]-2,3,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-ol

via PubChem

Wikidata facts

Mass: 428.402

Show 4 more facts

chemical formula: C₃₀H₅₂O
canonical SMILES: CC1C2CCC3C4CCC(C4(CCC3C2(CCC1O)C)C)C(C)C=C(C)C(C)C(C)C
isomeric SMILES: C[C@H]1[C@@H]2CC[C@H]3[C@@H]4CC[C@@H]([C@]4(CC[C@@H]3[C@]2(CC[C@@H]1O)C)C)[C@H](C)/C=C(\C)/[C@H](C)C(C)C
Commons category: Dinosterol

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Article

12 sections

Contents

Chemical structure
Biosynthesis
Biological occurrence
Preservation and diagenesis
Measurement techniques
Use as a biomarker
Dinosterol in a Marine Diatom
Phytoplankton Community in the Arabian Sea
Dinoflagellates in the Adriatic Sea
Dinoflagellates in the Arctic Ocean
Hydrogen Isotope Analysis
References

== Chemical structure == Dinosterol is a C30 sterol characterized by four fused rings (three six-membered and one five-membered), seven methyl groups, an olefin in its side-chain, and a secondary alcohol. The double bond in the side chain is located at the 22 position, and dinosterol's methyl groups are at the 20, 23, 24 and 25 positions of the side chain. The structure of dinosterol is established as 4α,23,24-trimethyl-5α-cholest-22-en-3β-ol.