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SMB00925

Sigma-Aldrich

5,6-trans-vitamin D3

≥90% (HPLC)

Sinónimos:

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

Fórmula empírica (notación de Hill):
C27H44O
Número de CAS:
Peso molecular:
384.64
Código UNSPSC:
12352205
NACRES:
NA.25

Nivel de calidad

Análisis

≥90% (HPLC)

formulario

solid

concentración

≤100%

color

white to pale yellow

temp. de almacenamiento

−20°C

cadena 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

Clave InChI

QYSXJUFSXHHAJI-YRZJJWOYSA-N

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Descripción general

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hydroxy seco-steroid that is (5Z,7E)-9,10-secocholesta-5,7,10(19)-triene in which the pro-S hydrogen at position 3 has been replaced by a hydroxy group.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

Aplicación

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

Características y beneficios

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

Otras notas

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

Pictogramas

Skull and crossbonesHealth hazard

Palabra de señalización

Danger

Frases de peligro

Clasificaciones de peligro

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

Código de clase de almacenamiento

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

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable


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Visite la Librería de documentos

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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