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30800 Sigma-Aldrich

7-Dehydrocholesterol

≥95.0% (HPLC)

Synonym: (−)-7-Dehydrocholesterol, 3β-Hydroxy-5,7-cholestadiene, 5,7-Cholestadien-3β-ol, Provitamin D3

  • CAS Number 434-16-2

  • Empirical Formula (Hill Notation) C27H44O

  • Molecular Weight 384.64

  •  Beilstein/REAXYS Number 2224615

  •  EC Number 207-100-5

  •  MDL number MFCD00003624

  •  eCl@ss 39023139

  •  PubChem Substance ID 57648485

  •  NACRES NA.79

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Properties

Related Categories Biochemicals and Reagents, Vitamin D, Vitamins More...
Quality Level   100
biological source   synthetic
assay   ≥95.0% (HPLC)
form   powder or crystals
optical activity   [α]20/D -115±8°, c = 1% in chloroform
color   white to faint yellow
mp   148-152 °C (lit.)
storage temp.   −20°C
SMILES string   [H][C@@]1(CC[C@@]2([H])C3=CC=C4C[C@@H](O)CC[C@]4(C)[C@@]3([H])CC[C@]12C)[C@H](C)CCCC(C)C
InChI   1S/C27H44O/c1-18(2)7-6-8-19(3)23-11-12-24-22-10-9-20-17-21(28)13-15-26(20,4)25(22)14-16-27(23,24)5/h9-10,18-19,21,23-25,28H,6-8,11-17H2,1-5H3/t19-,21+,23-,24+,25+,26+,27-/m1/s1
InChI key   UCTLRSWJYQTBFZ-DDPQNLDTSA-N

Description

General description

7-Dehydrocholesterol (7-DHC), a 5,7-conjugated diene sterol is a biosynthetic precursor of cholesterol. It helps in the production of vitamin D3 when exposed to ultraviolet B (UVB) radiation.

Application

7-Dehydrocholesterol has been used as an internal standard to determine sterols.

Biochem/physiol Actions

Down-regulates cholesterol biosynthesis in cultured Smith-Lemi-Opitz syndrome skin fibroblasts.

Other Notes

Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. 30800.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

Safety & Documentation

Safety Information

Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3

Documents

Certificate of Analysis (COA)

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Protocols & Articles

Articles

BACSMLS Online Plate Map

BACSMLS compounds are conveniently provided at 5µg per well, enough for multiple injections. These are high purity (>95%) compounds supplied in an economical, ready to use format. Compounds are arran...
Keywords: Metabolites

MSMLS Online Plate Map

Metabolite descriptors included with the software download upon purchase of the product include: Name, Parent CID, molecular formula, molecular weight, CAS, ChEBI, HMDB ID, PubChem Compound and Subst...
Keywords: Mass spectrometry, Metabolites

Vitamin D and Prevention of Human Disease

Vitamin D2 (ergocalciferol) is naturally synthesized from ergosterol by invertebrates, fungi, and plants in response to ultraviolet B irradiation, while vitamin D3 synthesis (cholecalciferol) is uniq...
Chloe McClanahan
BioFiles 2009, 4.6, 4.
Keywords: Absorption, Angiogenesis, Biofiles, Biological processes, Cancer, Clinical, Gene expression, Growth factors, Hormones, Hydroxylations, Ligands, Metabolites, Transcription, Type, Vitamins

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