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488577

Sigma-Aldrich

Cholesterol-2,2,3,4,4,6-d6

97 atom % D, 98% (CP)

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Synonym(s):
3β-Hydroxy-5-cholestene-2,2,3,4,4,5-d6, 5-Cholesten-3β-ol-2,2,3,4,4,5-d6, Deuterated cholesterol
Empirical Formula (Hill Notation):
C27D6H40O
CAS Number:
92543-08-3
Molecular Weight:
392.69
MDL number:
MFCD00209699
PubChem Substance ID:
24872407
NACRES:
NA.12

isotopic purity

97 atom % D

Assay

98% (CP)

optical activity

[α]20/D -40°, c = 2 in chloroform

technique(s)

mass spectrometry (MS): suitable

bp

360 °C (lit.)

mp

147-149 °C (lit.)

density

1.088 g/mL at 25 °C

mass shift

M+6

storage temp.

−20°C

SMILES string

[2H]C1=C2C([2H])([2H])[C@@]([2H])(O)C([2H])([2H])C[C@]2(C)[C@H]3CC[C@]4(C)[C@H](CC[C@H]4[C@@H]3C1)[C@H](C)CCCC(C)C

InChI

1S/C27H46O/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/h9,18-19,21-25,28H,6-8,10-17H2,1-5H3/t19-,21+,22+,23-,24+,25+,26+,27-/m1/s1/i9D,13D2,17D2,21D

InChI key

HVYWMOMLDIMFJA-HHPLMCQASA-N

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Packaging

This product may be available from bulk stock and can be packaged on demand. For information on pricing, availability and packaging, please contact Stable Isotopes Customer Service.

Storage Class Code

11 - Combustible Solids

WGK

WGK 1

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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S Giatti et al.
The Journal of steroid biochemistry and molecular biology, 199, 105596-105596 (2020-01-21)
Neuroactive steroids, molecules produced from cholesterol in steroidogenic cells (i.e., peripheral glands and nervous system) are physiological modulators and protective agents of nervous function. A possible role for neuroactive steroids in the sex-dimorphic clinical manifestation, onset and progression of Multiple
Matteo Ludovici et al.
Scientific reports, 8(1), 11500-11500 (2018-08-02)
The skin surface lipids (SSL) result from the blending of sebaceous and epidermal lipids, which derive from the sebaceous gland (SG) secretion and the permeability barrier of the stratum corneum (SC), respectively. In humans, the composition of the SSL is
David Wheeler et al.
Brain : a journal of neurology, 131(Pt 11), 3092-3102 (2008-09-06)
Maintaining the appropriate complement and content of lipids in cellular membranes is critical for normal neural function. Accumulating evidence suggests that even subtle perturbations in the lipid content of neurons and myelin can disrupt their function and may contribute to
Yasuyo Okada et al.
Carbohydrate research, 455, 54-61 (2017-11-25)
We aimed to investigate whether 6-O-α-maltosyl-β-cyclodextrin (Mal-βCD) is incorporated into cells and lysosomes during the release of unesterified cholesterol in Npc1-deficient Chinese hamster ovary (CHO) cells (Npc1 KO cells) and CHO-JP17 cells (JP17 cells). Internalization of Mal-βCD in cells and lysosomes and
Wenxu Zhou et al.
Journal of lipid research, 61(2), 192-204 (2019-09-25)
Primitive sterol evolution plays an important role in fossil record interpretation and offers potential therapeutic avenues for human disease resulting from nematode infections. Recognizing that C4-methyl stenol products [8(14)-lophenol] can be synthesized in bacteria while C4-methyl stanol products (dinosterol) can
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