Secalciferol

Names

[ Name ]:
Secalciferol

[Synonym ]:
k-dr
(3S,5Z,7E,14β,24R)-9,10-Secocholesta-5,7,10-triene-3,24,25-triol
Secalciferol
2,3-Heptanediol, 2-methyl-6-[(1R,3aR,4E,7aR)-octahydro-4-[(2Z)-2-[(5S)-5-hydroxy-2-methylenecyclohexylidene]ethylidene]-7a-methyl-1H-inden-1-yl]-, (3R,6R)-
osteod

Biological Activity

[Description]:

Secalciferol is a metabolite of Vitamin D, a possibly anti-inflammatory steroid which is involved in bone ossification. IC50 value:Target: In addition, it is known that Secalciferol mediates calcium and phosphorus homeostasis. Also Secalciferol inhibits calcium channels in osteosarcoma cells via suppressing the effects of 1α, 25-dihydroxyvitamin D3 and testosterone. Alternate studies indicate that Secalciferol can decrease the abundance of p53 and Pi-induced cytochrome c translocation. Furthermore, Secalciferol can increase cell proliferation in resting zone (RC) chondrocytes and inhibits matrix enzymes by possibly inhibiting the degradation of the matrix.

[Related Catalog]:

Signaling Pathways >> Vitamin D Related >> VD/VDR

Research Areas >> Inflammation/Immunology

[References]

[1]. Yamamoto T, Ozono K, Shima M, et al. 24R,25-dihydroxyvitamin D3 increases cyclic GMP contents, leading to an enhancement of osteocalcin synthesis by 1,25-dihydroxyvitamin D3 in cultured human osteoblastic cells. Exp Cell Res. 1998 Oct 10;244(1):71-6.

[2]. Sakaki T, Sawada N, Takeyama K, et al. Enzymatic properties of mouse 25-hydroxyvitamin D3 1 α-hydroxylase expressed in Escherichia coli. Eur J Biochem. 1999 Feb;259(3):731-8.

[3]. Norman AW, Okamura WH, Bishop JE, Henry HL. Update on biological actions of 1α,25(OH)2-vitamin D3 (rapid effects) and 24R,25(OH)2-vitamin D3. Mol Cell Endocrinol. 2002 Nov 29;197(1-2):1-13

[4]. Hurst-Kennedy J, Zhong M, Gupta V et al. 24R,25-Dihydroxyvitamin D3, lysophosphatidic acid, and p53: a signaling axis in the inhibition of phosphate-induced chondrocyte apoptosis. J Steroid Biochem Mol Biol. 2010 Oct;122(4):264-71.

[5]. Wehmeier KR, Alamir AR, Sultan S, et al. 24, 25-dihydroxycholecalciferol but not 25-hydroxycholecalciferol suppresses apolipoprotein A-I gene expression. Life Sci. 2011 Jan 3;88(1-2):110-6.

[6]. Rubin LP, Yeung B, Vouros P et al. Evidence for human placental synthesis of 24,25-dihydroxyvitamin D3 and 23,25-dihydroxyvitamin D3. Pediatr Res. 1993 Jul;34(1):98-104.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.1±0.1 g/cm3

[ Boiling Point ]:
571.1±35.0 °C at 760 mmHg

[ Melting Point ]:
63-65ºC

[ Molecular Formula ]:
C₂₇H₄₄O₃

[ Molecular Weight ]:
416.637

[ Flash Point ]:
241.5±20.5 °C

[ Exact Mass ]:
416.329041

[ PSA ]:
60.69000

[ LogP ]:
5.85

[ Vapour Pressure ]:
0.0±3.6 mmHg at 25°C

[ Index of Refraction ]:
1.547

[ Storage condition ]:
2-8℃

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: VS2895000

CHEMICAL NAME :: 9,10-Secocholesta-5,7,10(19)-triene-3,24,25-triol, (3-beta,5Z,7E,24R)-

CAS REGISTRY NUMBER :: 55721-11-4

LAST UPDATED :: 199512

DATA ITEMS CITED :: 2

MOLECULAR FORMULA :: C27-H44-O3

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >10 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JKXXAF Japanese Kokai Tokyo Koho Patents. (U.S. Patent and Trademark Office, Foreign Patents, Washington, DC 20231) Volume(issue)/page/year: #94-247858

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >2 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: JKXXAF Japanese Kokai Tokyo Koho Patents. (U.S. Patent and Trademark Office, Foreign Patents, Washington, DC 20231) Volume(issue)/page/year: #94-247858

Safety Information

[ Symbol ]:

GHS06, GHS08

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H301 + H311-H330-H372

[ Precautionary Statements ]:
P260-P280-P284-P301 + P310-P310

[ Personal Protective Equipment ]:
Eyeshields;Faceshields;full-face particle respirator type N100 (US);Gloves;respirator cartridge type N100 (US);type P1 (EN143) respirator filter;type P3 (EN 143) respirator cartridges

[ Hazard Codes ]:
T+:Verytoxic;

[ Risk Phrases ]:
R28

[ Safety Phrases ]:
S28-S36/37-S45

[ RIDADR ]:
UN 2811

[ RTECS ]:
VS2895000

Synthetic Route

Click to get detail synthetic route

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