WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 463109
CAS#: 22350-41-0
Description: 5,6-trans-Vitamin D3 is an isomer of vitamin D3. In vivo, 5,6-trans-vitamin D3 increases tibia ash weight and bone mineralization in vitamin D-deficient chicks. 5,6-trans-Vitamin D3 induces intestinal calcium transport and bone calcium mobilization in anephric rats fed a low-calcium and vitamin D-deficient diet.
MedKoo Cat#: 463109
Name: 5,6-trans-Vitamin D3
CAS#: 22350-41-0
Chemical Formula: C27H44O
Exact Mass: 384.3392
Molecular Weight: 384.648
Elemental Analysis: C, 84.31; H, 11.53; O, 4.16
Synonym: 5,6-trans-Vitamin D3; 5,6-trans-Cholecalciferol;
IUPAC/Chemical Name: (S,E)-3-(2-((1R,3aS,7aR,E)-7a-methyl-1-((R)-6-methylheptan-2-yl)octahydro-4H-inden-4-ylidene)ethylidene)-4-methylenecyclohexan-1-ol
InChi Key: QYSXJUFSXHHAJI-FVUVGDFOSA-N
InChi Code: 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
SMILES Code: C=C1CC[C@@H](C/C1=C\C=C2CCC[C@]3([C@]/2(CC[C@@]3([C@H](C)CCCC(C)C)[H])[H])C)O
Appearance: Solid powder
Purity: >98% (or refer to the Certificate of Analysis)
Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility: Soluble in DMSO
Shelf Life: >3 years if stored properly
Drug Formulation: This drug may be formulated in DMSO
Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code: 2934.99.9001
The following data is based on the product molecular weight 384.648 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass | 1 mg | 5 mg | 10 mg |
|---|---|---|---|
| 1 mM | 1.15 mL | 5.76 mL | 11.51 mL |
| 5 mM | 0.23 mL | 1.15 mL | 2.3 mL |
| 10 mM | 0.12 mL | 0.58 mL | 1.15 mL |
| 50 mM | 0.02 mL | 0.12 mL | 0.23 mL |
1: Scurachio RS, Santos WG, Nascimento ES, Skibsted LH, Cardoso DR. Isomerization of Cholecalciferol through Energy Transfer as a Protective Mechanism Against Flavin-Sensitized Photooxidation. J Agric Food Chem. 2015 May 13;63(18):4629-37. doi: 10.1021/jf505958c. Epub 2015 Apr 29. PMID: 25891983.
2: Wojtkielewicz A, Morzycki JW. Synthesis of gamma- and delta-lactones from 1alpha-hydroxy-5,6-trans-vitamin D3 by ring-closing metathesis route and their reduction with metal hydrides. Steroids. 2007 Jun;72(6-7):552-8. doi: 10.1016/j.steroids.2007.03.005. Epub 2007 Mar 18. PMID: 17493648.
3: Swami S, Zhao XY, Sarabia S, Siu-Caldera ML, Uskokovic M, Reddy SG, Feldman D. A low-calcemic vitamin D analog (Ro 25-4020) inhibits the growth of LNCaP human prostate cancer cells with increased potency by producing an active 24-oxo metabolite (Ro 29-9970). Recent Results Cancer Res. 2003;164:349-52. doi: 10.1007/978-3-642-55580-0_24. PMID: 12899533.
4: Chen TC, Persons KS, Lu Z, Mathieu JS, Holick MF. An evaluation of the biologic activity and vitamin D receptor binding affinity of the photoisomers of vitamin D3 and previtamin D3. J Nutr Biochem. 2000 May;11(5):267-72. doi: 10.1016/s0955-2863(00)00077-2. PMID: 10876100.
5: Wecksler WR, Norman AW. Studies on the mode of action of calciferol XXV. 1 alpha,25-dihydroxy-5,6-trans-vitamin D3, the 5E-isomer of 1 alpha,25-dihydroxyvitamin D3. Steroids. 1980 Apr;35(4):419-25. doi: 10.1016/0039-128x(80)90142-7. PMID: 6246662.
6: Mouriño A, Blair P, Wecksler W, Johnson RL, Norman AW, Okamura WH. Studies on vitamin D (calciferol) and its analogues. 15. 24-Nor-1alpha,25-dihydroxyvitamin D3 and 24-nor-25-hydroxy-5,6-trans-vitamin D3. J Med Chem. 1978 Oct;21(10):1025-9. doi: 10.1021/jm00208a005. PMID: 214553.
7: Hofsass H, Alicino NJ, Hirsch AL, Ameika L, Smith LD. Comparison of high pressure liquid chromatographic and chemical methods for vitamin D3 concentrates. II. Collaborative study. J Assoc Off Anal Chem. 1978 May;61(3):735-45. PMID: 206533.
8: Borsje B, Heyting A, Roborgh JR, Ross DB, Shillam KW. Analysis of fat-soluble vitamins. XVI. Antirachitic activity of 5,6-trans-vitamin D3 alone and in the presence of 5,6-cis-vitamin D3 resin, using chick bioassays. J Assoc Off Anal Chem. 1977 Sep;60(5):1003-9. PMID: 197056.
9: Okamura WH, Hammond ML, Rego A, Norman AW, Wing RM. Studies on vitamin D (calciferol) and its analogues. 12. Structural and synthetic studies of 5,6-trans-vitamin D3 and the stereoisomers of 10,19-dihydrovitamin D3 including dihydrotachysterol3. J Org Chem. 1977 Jun 24;42(13):2284-91. doi: 10.1021/jo00433a021. PMID: 195026.
10: Kobayashi T, Moriuchi S, Shimura F, Katsui G. Synthesis and biological activity of 5,6-trans-vitamin D3 in anephric rats. J Nutr Sci Vitaminol (Tokyo). 1976;22(4):299-306. doi: 10.3177/jnsv.22.299. PMID: 189003.
11: Stern PH, Trummel CL, Schnoes HK, Deluca HF. Bone resorbing activity of vitamin D metabolites and congeners in vitro: influence of hydroxyl substituents in the A ring. Endocrinology. 1975 Dec;97(6):1552-8. doi: 10.1210/endo-97-6-1552. PMID: 1204577.
12: Rutherford WE, Hruska K, Blondin J, Holick M, DeLuca H, Klahr S, Slatopolsky E. The effect of 5,6-trans vitamin D3 on calcium absorption in chronic renal disease. J Clin Endocrinol Metab. 1975 Jan;40(1):13-18. doi: 10.1210/jcem-40-1-13. PMID: 1112871.
13: Tsukida K, Akutsu K, Saiki K. Carbon-13 nuclear magnetic resonance spectra of vitamins D and related compounds. J Nutr Sci Vitaminol (Tokyo). 1975;21(6):411-20. doi: 10.3177/jnsv.21.411. PMID: 178846.
14: Gagnon R, Ogden GW, Just G, Kaye M. Comparison of dihydrotachysterol and 5,6-trans vitamin D3 on intestinal calcium absorption in patients with chronic renal failure. Can J Physiol Pharmacol. 1974 Apr;52(2):272-4. doi: 10.1139/y74-037. PMID: 4365509.
