Sitocalciférol

Identification
Sitocalciférol

Nom UICPA	(1S,3Z)-3-[(2E)-2-[(1R,3aS,7aR)-1-[(1R,4S)-4-éthyl-1,5-diméthylhexyl]-7a-méthyl-2,3,3a,5,6,7-hexahydro-1H-inden-4-ylidène]éthylidène]-4-méthylène-1-cyclohexanol
Synonymes	Vitamine D5 24-éthylcholécalciférol
N^o CAS	71761-06-3
PubChem	(en) « Sitocalciférol », sur PubChem
ChEBI	33279
SMILES	[H][C@@]1(CC[C@@]2([H])C(\CCC[C@]12C)=C\C=C3\C[C@@H](O)CCC3=C)[C@H](C)CC[C@@H](CC)C(C)C PubChem, vue 3D
InChI	InChI : vue 3D InChI=1/C29H48O/c1-7-23(20(2)3)12-10-22(5)27-16-17-28-24(9-8-18-29(27,28)6)13-14-25-19-26(30)15-11-21(25)4/h13-14,20,22-23,26-28,30H,4,7-12,15-19H2,1-3,5-6H3/b24-13+,25-14-/t22-,23-,26+,27-,28+,29-/m1/s1
Propriétés chimiques
Formule	C₂₉H₄₈O [Isomères]
Masse molaire^[1]	412,690 8 ± 0,026 9 g/mol C 84,4 %, H 11,72 %, O 3,88 %, 412.69082
Propriétés physiques
T° fusion	517 °C
Point d’éclair	225,1 °C

Unités du SI et CNTP, sauf indication contraire.
modifier

Le sitocalciférol, également appelé vitamine D₅, est une forme de vitamine D découverte en 1936 par W. Wunderlich^[2]. Il est biosynthétisé à partir du 7-déshydrositostérol, et peut être obtenu à partir du β-sitostérol par synthèse organique.

Des analogues synthétiques du sitocalciférol ont été proposés comme étant de potentiels agents antitumoraux^[3]^,^[4]^,^[5].

Voir aussi

Références

↑ Masse molaire calculée d’après « Atomic weights of the elements 2007 », sur www.chem.qmul.ac.uk.
↑ (en) W. Wunderlich, « Hoppe-Seyler's Z. Physiol. Chem. », 1936, vol. 241, p. 116-124.
↑ (en) R. G. Mehta, R. M. Moriarty, R. R. Mehta et al., « Prevention of preneoplastic mammary lesion development by a novel vitamin D analogue, 1alpha-hydroxyvitamin D5 », J Natl Cancer Inst, vol. 89, n^o 3,‎ février 1997, p. 212-218. (PMID 9017001, DOI 10.1093/jnci/89.3.212, lire en ligne)
↑ (en) G. Murillo et R. G. Mehta, « Chemoprevention of chemically-induced mammary and colon carcinogenesis by 1alpha-hydroxyvitamin D5 », J. Steroid Biochem. Mol. Biol., vol. 97, n^os 1-2,‎ octobre 2005, p. 129–36. (PMID 16051482, DOI 10.1016/j.jsbmb.2005.06.008, lire en ligne)
↑ (en) R.G. Mehta, « Stage-specific inhibition of mammary carcinogenesis by 1alpha-hydroxyvitamin D5 », Eur. J. Cancer, vol. 40, n^o 15,‎ octobre 2004, p. 2331-2337 (PMID 15454260, DOI 10.1016/j.ejca.2004.05.025, lire en ligne)

v · m

Vitamines

Liposolubles

A	Rétinol Rétinal Trétinoïne Carotène α β Hypervitaminose A
D	D₂ Ergocalciférol D₃ Cholécalciférol 7-Déshydrocholestérol Calcitriol D₄ Dihydroergocalciférol D₅ Sitocalciférol Hypervitaminose D
E	Tocophérol α β γ δ Tocotriénol α β γ δ Hypervitaminose E
K	K₁ Phylloquinone K₂ Ménaquinone Ménatétrénone K₃ Ménadione K₄ Ménadiol Naphtoquinone

Hydrosolubles

B	B₁ Thiamine B₂ Riboflavine B₃ Niacine Nicotinamide B₅ Acide pantothénique B₆ Pyridoxine Pyridoxal Pyridoxamine B₈ Biotine B₉ Acide folique Acide dihydrofolique B₁₂ Cyano- Hydroxo- Méthyl- Adénosyl- Cobalamines
C	Acide ascorbique Na Ca Palmitate Stéarate Acide déshydroascorbique

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