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MilliporeSigma

30800

7-Dehydrocholesterol

≥95.0% (HPLC)

Synonym(s):

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

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5 G

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About This Item

Empirical Formula (Hill Notation):
C27H44O
CAS Number:
434-16-2
Molecular Weight:
384.64
NACRES:
NA.79
PubChem Substance ID:
57648485
eCl@ss:
39023139
UNSPSC Code:
12352211
EC Number:
207-100-5
MDL number:
MFCD00003624
Beilstein/REAXYS Number:
2224615

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InChI key

UCTLRSWJYQTBFZ-DDPQNLDTSA-N

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

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

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

Quality Level

100

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1 of 4

This Item
C9774C1357774898
7-Dehydrocholesterol ≥95.0% (HPLC)

Sigma-Aldrich

30800

7-Dehydrocholesterol

Cholecalciferol analytical standard

Sigma-Aldrich

C9774

Cholecalciferol

Cholecalciferol meets USP testing specifications

Sigma-Aldrich

C1357

Cholecalciferol

7-Dehydrocholesterol-25,26,26,26,27,27,27-d7 ≥99 atom % D, ≥98% (CP)

Sigma-Aldrich

774898

7-Dehydrocholesterol-25,26,26,26,27,27,27-d7

biological source

synthetic

biological source

synthetic (organic - wool)

biological source

-

biological source

-

assay

≥95.0% (HPLC)

assay

≥97.0%

assay

97.0-103.0%

assay

≥98% (CP)

form

powder or crystals

form

crystalline

form

crystalline

form

solid

storage temp.

−20°C

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

−20°C

color

white to faint yellow

color

white

color

white

color

-

mp

148-152 °C (lit.)

mp

83-86 °C (lit.)

mp

83-86 °C (lit.)

mp

-

General description

7-Dehydrocholesterol (7-DHC), a 5,7-conjugated diene sterol is a biosynthetic precursor of cholesterol.[1] It helps in the production of vitamin D3 when exposed to ultraviolet B (UVB) radiation.[2]

Application

7-Dehydrocholesterol has been used as an internal standard to determine sterols.[3]

Biochem/physiol Actions

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

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
BCCN3140
BCCK9520
BCCL8081
BCCJ4317
BCCG8559

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7-Dehydrocholesterol (7-DHC), But Not Cholesterol, Causes Suppression of Canonical TGF-beta Signaling and Is Likely Involved in the Development of Atherosclerotic Cardiovascular Disease (ASCVD)
Huang SS, et al.
Journal of Cellular Biochemistry, 118(6), 1387-1387 (2017)
Amaranth oil increased fecal excretion of bile acid but had no effect in reducing plasma cholesterol in hamsters
de Castro lIA, et al.
Lipids, 48, 609-618 (2013)
Vitamin D, Calcium, and the Epidermis
Vitamin D, 1, 527-544 (2018)
Daniele Silvestro et al.
Scientific reports, 8(1), 16348-16348 (2018-11-07)
Vitamin D3 is a secosterol hormone critical for bone growth and calcium homeostasis, produced in vertebrate skin by photolytic conversion of the cholesterol biosynthetic intermediate provitamin D3. Insufficient levels of vitamin D3 especially in the case of low solar UV-B
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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