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D4429

Sigma-Aldrich

7-Dehydrocholesterin

≥85%

Synonym(e):

(−)-7-Dehydrocholesterin, 3β-Hydroxy-5,7-cholestadien, 5,7-Cholestadien-3β-ol, Provitamin D3

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About This Item

Empirische Formel (Hill-System):
C27H44O
CAS-Nummer:
434-16-2
Molekulargewicht:
384.64
Beilstein:
2224615
EG-Nummer:
207-100-5
MDL-Nummer:
MFCD00003624
UNSPSC-Code:
12352200
eCl@ss:
39023139
PubChem Substanz-ID:
24893874

Assay

≥85%

mp (Schmelzpunkt)

148-152 °C (lit.)

Lagertemp.

−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

InChIKey

UCTLRSWJYQTBFZ-DDPQNLDTSA-N

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Biochem./physiol. Wirkung

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

Verlinkung

Do not confuse with dihydrocholesterol.

Lagerklassenschlüssel

13 - Non Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

Eyeshields, Gloves, type N95 (US)

Analysenzertifikate (COA)

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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
Małgorzata J M Nowaczyk et al.
American journal of medical genetics. Part C, Seminars in medical genetics, 160C(4), 250-262 (2012-10-13)
Smith-Lemli-Opitz syndrome (SLOS) is a congenital multiple anomaly/intellectual disability syndrome caused by a deficiency of cholesterol synthesis resulting from a deficiency of 7-dehydrocholesterol (7DHC) reductase encoded by DHCR7. SLOS is inherited in an autosomal recessive pattern. It is characterized by
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
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