D4429
7-Dehydrocholesterol
≥85%
Synonym(s):
(−)-7-Dehydrocholesterol, 3β-Hydroxy-5,7-cholestadiene, 5,7-Cholestadien-3β-ol, Provitamin D3
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About This Item
Empirical Formula (Hill Notation):
C27H44O
CAS Number:
Molecular Weight:
384.64
UNSPSC Code:
12352200
PubChem Substance ID:
eCl@ss:
39023139
EC Number:
207-100-5
Beilstein/REAXYS Number:
2224615
MDL number:
assay
≥85%
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
Biochem/physiol Actions
Down-regulates cholesterol biosynthesis in cultured Smith-Lemi-Opitz syndrome skin fibroblasts.
Other Notes
Do not confuse with dihydrocholesterol.
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Storage Class
13 - Non Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
Regulatory Information
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Zeljka Korade et al.
Journal of inherited metabolic disease, 36(1), 113-122 (2012-06-22)
7-Dehydrocholesterol (7-DHC) accumulates in tissues and fluids of patients with Smith-Lemli-Opitz syndrome (SLOS), which is caused by mutations in the gene encoding 3β-hydroxysterol-Δ(7)-reductase (DHCR7). We recently reported that 7-DHC is the most reactive lipid molecule toward free radical oxidation (lipid
Michael Lang et al.
Science (New York, N.Y.), 337(6102), 1658-1661 (2012-09-29)
Most living species exploit a limited range of resources. However, little is known about how tight associations build up during evolution between such specialist species and the hosts they use. We examined the dependence of Drosophila pachea on its single
P E Jira et al.
Journal of lipid research, 41(8), 1339-1346 (2000-08-18)
The Smith-Lemli-Opitz syndrome (SLOS) is caused by deficient Delta(7)-dehydrocholesterol reductase, which catalyzes the final step of the cholesterol biosynthetic pathway, resulting in low cholesterol and high concentrations of its direct precursors 7-dehydrocholesterol (7DHC) and 8DHC. We hypothesized that i) 7DHC