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D4429

Sigma-Aldrich

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:
434-16-2
Molecular Weight:
384.64
Beilstein:
2224615
EC Number:
207-100-5
MDL number:
MFCD00003624
UNSPSC Code:
12352200
eCl@ss:
39023139
PubChem Substance ID:
24893874

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

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Biochem/physiol Actions

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

Linkage

Do not confuse with dihydrocholesterol.

Storage Class Code

13 - Non Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
BCBQ3252V
BCBN4729V
BCBG8316V
1431250V
1431250

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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
M Satué et al.
Acta biomaterialia, 9(3), 5759-5770 (2012-12-04)
Vitamin D plays a central role in bone regeneration, and its insufficiency has been reported to have profound negative effects on implant osseointegration. The present study aimed to test the in vitro biological effect of titanium (Ti) implants coated with
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
A Jezela-Stanek et al.
Clinical genetics, 69(1), 77-85 (2006-02-03)
Smith-Lemli-Opitz syndrome (SLOS) is an autosomal recessive disorder caused by reduced activity of 7-dehydrocholesterol (7DHC) reductase, resulting in a decreased level of cholesterol and increased concentrations of 7DHC and 8DHC in body fluids and tissues. Ten pregnancies at 25% risk
B Lehmann et al.
The Journal of investigative dermatology, 117(5), 1179-1185 (2001-11-17)
We have previously shown that keratinocytes in vitro can convert biologically inactive vitamin D3 to the hormone calcitriol (1alpha,25-dihydroxyvitamin D3). This study was initiated to test whether the ultraviolet-B-induced photolysis of provitamin D3 (7-dehydrocholesterol), which results in the formation of
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