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SMB00925

Sigma-Aldrich

5,6-trans-vitamin D3

≥90% (HPLC)

Synonym(s):

5,6-trans-vitamin D3, (3b,5E,7E)-9,10-Secocholesta-5,7,10(19)-trien-3-ol, calciol, cholecalciferol, colecalciferol

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About This Item

Empirical Formula (Hill Notation):
C27H44O
CAS Number:
22350-41-0
Molecular Weight:
384.64
UNSPSC Code:
12352205
NACRES:
NA.25

Quality Level

100

Assay

≥90% (HPLC)

form

solid

concentration

≤100%

color

white to pale yellow

storage temp.

−20°C

SMILES string

Canonical: CC(C)CCCC(C)C1CCC2C1(CCCC2=CC=C3CC(CCC3=C)O)CIsomeric:C[C@H](CCCC(C)C)[C@H]1CC[C@@H]\2[C@@]1(CCC/C2=C\C=C\3/C[C@H](CCC3=C)O)C

InChI

1S/C27H44O/c1-19(2)8-6-9-21(4)25-15-16-26-22(10-7-17-27(25,26)5)12-13-23-18-24(28)14-11-20(23)3/h12-13,19,21,24-26,28H,3,6-11,14-18H2,1-2,4-5H3/b22-12+,23-13-/t21-,24+,25-,26+,27-/m1/s1

InChI key

QYSXJUFSXHHAJI-YRZJJWOYSA-N

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General description

Calciol is a hydroxy seco-steroid that is (5Z,7E)-9,10-secocholesta-5,7,10(19)-triene in which the pro-S hydrogen at position 3 has been replaced by a hydroxy group. It is the inactive form of vitamin D3, being hydroxylated in the liver to calcidiol (25-hydroxyvitamin D3), which is then further hydroxylated in the kidney to give calcitriol (1,25-dihydroxyvitamin D3), the active hormone. It has a role as a human metabolite. It is a seco-cholestane, a hydroxy seco-steroid, a member of D3 vitamins, a secondary alcohol and a steroid hormone.

Also known as 5,6-trans-Cholecalciferol, this compound is the major photoisomer of the Vitamin D3 analog and acts as a biologically active form of cholecalciferol (vitamin D). Vitamin D3 induces cell differentiation and prevents the proliferation of cancer cells. Additionally, 5,6-trans-Cholecalciferol activates calcium-dependent signaling pathways crucial for bone metabolism and the immune system. It is a versatile molecule with hypoglycemic and anti-inflammatory properties, making it applicable in immunology, oncology, metabolomics, and biochemical research.

Application

5,6-trans-vitamin D3 has been used:
  • to study the effects of different derivatives of vitamin D3 on bone resorption
  • to study the antiproliferative activity of photoisomers

Features and Benefits

  • Can be used in Metabolomics and Biochemical research
  • High-quality compound suitable for multiple research applications

Other Notes

For additional information on our range of Biochemicals, please complete this form.

Pictograms

Skull and crossbonesHealth hazard
GHS06,GHS08

Signal Word

Danger

Hazard Statements

H300 + H310 + H330,H372

Hazard Classifications

Acute Tox. 2 Dermal - Acute Tox. 2 Inhalation - Acute Tox. 2 Oral - STOT RE 1

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Regulatory Information

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Bone resorbing activity of vitamin D metabolites and congeners in vitro: influence of hydroxyl substituents in the A ring
Stern PH et al.
Endocrinology, 97, 1552-1558 (1975)
An evaluation of the biologic activity and vitamin D receptor binding affinity of the photoisomers of vitamin D3 and previtamin D3
Chen TC
The Journal of Nutritional Biochemistry, 11, 267-272 (2000)

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