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Merck
CN

SMB00925

5,6-trans-vitamin D3

≥90% (HPLC)

别名:

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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关于此项目

经验公式（希尔记法）:
C27H44O
化学文摘社编号:
22350-41-0
分子量:
384.64
UNSPSC Code:
12352205
NACRES:
NA.25

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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

assay

≥90% (HPLC)

form

solid

concentration

≤100%

color

white to pale yellow

storage temp.

−20°C

Quality Level

100

相关类别

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hydroxy seco-steroid that is (5Z,7E)-9,10-secocholesta-5,7,10(19)-triene in which the pro-S hydrogen at position 3 has been replaced by a hydroxy group.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

signalword

Danger

Hazard Classifications

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

存储类别

6.1A - Combustible acute toxic Cat. 1 and 2 / very toxic hazardous materials

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

法规信息

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分析证书(COA)

Lot/Batch Number
0000482794
0000482794
0000444392
0000444392
0000374941

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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)
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)

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