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SMB00925

Sigma-Aldrich

5,6-trans-vitamin D3

≥90% (HPLC)

Synonyme(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

Formule empirique (notation de Hill):
C27H44O
Numéro CAS:
Poids moléculaire :
384.64
Code UNSPSC :
12352205
Nomenclature NACRES :
NA.25

Niveau de qualité

Pureté

≥90% (HPLC)

Forme

solid

Concentration

≤100%

Couleur

white to pale yellow

Température de stockage

−20°C

Chaîne SMILES 

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

Clé InChI

QYSXJUFSXHHAJI-YRZJJWOYSA-N

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Description générale

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hydroxy seco-steroid that is (5Z,7E)-9,10-secocholesta-5,7,10(19)-triene in which the pro-S hydrogen at position 3 has been replaced by a hydroxy group.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

Caractéristiques et avantages

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

Autres remarques

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Pictogrammes

Skull and crossbonesHealth hazard

Mention d'avertissement

Danger

Mentions de danger

Classification des risques

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

Code de la classe de stockage

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

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable


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Consulter la Bibliothèque de documents

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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