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55721-11-4,MFCD00941417
Catalog No.:AA00DB4N

55721-11-4 | Secalciferol

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1mg
≥98% (vitamin + pre-vitamin)
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$6,129.00   $4,290.00
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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA00DB4N
Chemical Name:
Secalciferol
CAS Number:
55721-11-4
Molecular Formula:
C27H44O3
Molecular Weight:
416.6365
MDL Number:
MFCD00941417
SMILES:
O[C@H]1CCC(=C)/C(=C\C=C\2/CCC[C@]3([C@H]2CC[C@@H]3[C@@H](CC[C@H](C(O)(C)C)O)C)C)/C1
Properties
Computed Properties
 
Complexity:
688  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
6  
Defined Bond Stereocenter Count:
2  
Heavy Atom Count:
30  
Hydrogen Bond Acceptor Count:
3  
Hydrogen Bond Donor Count:
3  
Rotatable Bond Count:
6  
XLogP3:
5  

Literature

Title: Motor neuron-like NSC-34 cells as a new model for the study of vitamin D metabolism in the brain.

Journal: The Journal of steroid biochemistry and molecular biology 20160401

Title: Enhancement of vitamin D metabolites in the eye following vitamin D3 supplementation and UV-B irradiation.

Journal: Current eye research 20121001

Title: Expression of human CYP27B1 in Escherichia coli and characterization in phospholipid vesicles.

Journal: The FEBS journal 20121001

Title: Serum 24,25-dihydroxyvitamin D concentrations in osteogenesis imperfecta: relationship to bone parameters.

Journal: The Journal of clinical endocrinology and metabolism 20120401

Title: Hypercalcemia, hypercalciuria, and elevated calcitriol concentrations with autosomal dominant transmission due to CYP24A1 mutations: effects of ketoconazole therapy.

Journal: The Journal of clinical endocrinology and metabolism 20120301

Title: Simultaneous measurement of plasma vitamin D(3) metabolites, including 4β,25-dihydroxyvitamin D(3), using liquid chromatography-tandem mass spectrometry.

Journal: Analytical biochemistry 20111101

Title: The ratio of serum 24,25-dihydroxyvitamin D(3) to 25-hydroxyvitamin D(3) is predictive of 25-hydroxyvitamin D(3) response to vitamin D(3) supplementation.

Journal: The Journal of steroid biochemistry and molecular biology 20110901

Title: Regulation of vitamin D metabolism.

Journal: Best practice & research. Clinical endocrinology & metabolism 20110801

Title: Short-term individual nutritional care as part of routine clinical setting improves outcome and quality of life in malnourished medical patients.

Journal: Clinical nutrition (Edinburgh, Scotland) 20110401

Title: Vitamin D metabolites are associated with clinical and MRI outcomes in multiple sclerosis patients.

Journal: Journal of neurology, neurosurgery, and psychiatry 20110201

Title: 24, 25-dihydroxycholecalciferol but not 25-hydroxycholecalciferol suppresses apolipoprotein A-I gene expression.

Journal: Life sciences 20110103

Title: Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: novel antibacterial agents against Mycobacterium tuberculosis.

Journal: Bioorganic & medicinal chemistry letters 20101101

Title: 24R,25-Dihydroxyvitamin D3, lysophosphatidic acid, and p53: a signaling axis in the inhibition of phosphate-induced chondrocyte apoptosis.

Journal: The Journal of steroid biochemistry and molecular biology 20101001

Title: 24R,25-dihydroxyvitamin D3 [24R,25(OH)2D3] controls growth plate development by inhibiting apoptosis in the reserve zone and stimulating response to 1alpha,25(OH)2D3 in hypertrophic cells.

Journal: The Journal of steroid biochemistry and molecular biology 20100701

Title: A short practical approach to 24R,25-dihydroxyvitamin D3.

Journal: The Journal of steroid biochemistry and molecular biology 20100701

Title: Metabolism of substrates incorporated into phospholipid vesicles by mouse 25-hydroxyvitamin D3 1alpha-hydroxylase (CYP27B1).

Journal: The Journal of steroid biochemistry and molecular biology 20100401

Title: 25-Hydroxyvitamin D(3) is an agonistic vitamin D receptor ligand.

Journal: The Journal of steroid biochemistry and molecular biology 20100215

Title: Plasma 25-hydroxycholecalciferol and 1,25-dihydroxycholecalciferol concentrations are decreased in hind limb unloaded Dahl salt-sensitive female rats.

Journal: The Journal of steroid biochemistry and molecular biology 20100215

Title: Lysophosphatidic acid signaling promotes proliferation, differentiation, and cell survival in rat growth plate chondrocytes.

Journal: Biochimica et biophysica acta 20090501

Title: Inorganic phosphate modulates responsiveness to 24,25(OH)2D3 in chondrogenic ATDC5 cells.

Journal: Journal of cellular biochemistry 20090501

Title: A kinetic overview of the receptors involved in 1,25-dihydroxyvitamin D3 and 24,25-dihydroxyvitamin D3 signaling: a systems biology approach.

Journal: Critical reviews in eukaryotic gene expression 20090101

Title: Prevention of rickets and vitamin D deficiency in infants, children, and adolescents.

Journal: Pediatrics 20081101

Title: Expression and regulation of the vitamin D receptor in the zebrafish, Danio rerio.

Journal: Journal of bone and mineral research : the official journal of the American Society for Bone and Mineral Research 20080901

Title: Inappropriate serum levels of retinol, alpha-tocopherol, 25 hydroxyvitamin D3 and 24,25 dihydroxyvitamin D3 levels in healthy Spanish adults: simultaneous assessment by HPLC.

Journal: Clinical biochemistry 20080601

Title: 1,25(OH)2-vitamin D3 inhibits proliferation and decreases production of monocyte chemoattractant protein-1, thrombopoietin, VEGF, and angiogenin by human annulus cells in vitro.

Journal: Spine 20080401

Title: Contemporary diagnosis and treatment of vitamin D-related disorders.

Journal: Journal of bone and mineral research : the official journal of the American Society for Bone and Mineral Research 20071201

Title: Contributions of pro-oxidant and anti-oxidant conditions to the actions of 24,25-dihydroxyvitamin D3 and 1,25-dihydroxyvitamin D3 on phosphate uptake in intestinal cells.

Journal: Journal of cellular biochemistry 20070801

Title: Phosphate uptake in chick kidney cells: effects of 1,25(OH)2D3 and 24,25(OH)2D3.

Journal: Steroids 20070201

Title: Environmental salinity regulates the in vitro production of [3H]-1,25-dihydroxyvitamin D3 and [3H]-24,25 dihydroxyvitamin D3 in rainbow trout (Oncorhynchus mykiss).

Journal: General and comparative endocrinology 20070101

Title: Membrane receptors for vitamin D metabolites.

Journal: Critical reviews in eukaryotic gene expression 20070101

Title: Functional evolution of the vitamin D and pregnane X receptors.

Journal: BMC evolutionary biology 20070101

Title: Changes in vitamin D after gastrectomy.

Journal: Gastric cancer : official journal of the International Gastric Cancer Association and the Japanese Gastric Cancer Association 20070101

Title: Mechanism of 24,25-dihydroxyvitamin D3-mediated inhibition of rapid, 1,25-dihydroxyvitamin D3-induced responses: role of reactive oxygen species.

Journal: Journal of cellular biochemistry 20061215

Title: Role of dihydroxyvitamin D(3) and its nuclear receptor in novel directed therapies for cancer.

Journal: General physiology and biophysics 20061201

Title: Evidence that both 1alpha,25-dihydroxyvitamin D3 and 24-hydroxylated D3 enhance human osteoblast differentiation and mineralization.

Journal: Journal of cellular biochemistry 20061015

Title: Effects of 24R,25- and 1alpha,25-dihydroxyvitamin D3 on mineralizing growth plate chondrocytes.

Journal: Journal of cellular biochemistry 20060515

Title: Regulation of parathyroid hypertensive factor secretion by vitamin D3 analogs in parathyroid cells derived from spontaneously hypertensive rats.

Journal: Journal of cellular biochemistry 20050901

Title: Thrombin peptide (TP508) treatment of rat growth plate cartilage cells promotes proliferation and retention of the chondrocytic phenotype while blocking terminal endochondral differentiation.

Journal: Journal of cellular physiology 20050201

Title: [Comparative study 1,25-dihydroxycholecalciferols and 24,25-dihydroxycholecalciferols effect on ionized calcium level in blood plasma of patients with osteoporosis].

Journal: Voprosy pitaniia 20050101

Title: Analysis of C-3 epimerization in (24R)-24,25-dihydroxyvitamin D3 catalyzed by hydroxysteroid dehydrogenase.

Journal: Journal of pharmaceutical and biomedical analysis 20041115

Title: The role of Vitamin D3 metabolism in prostate cancer.

Journal: The Journal of steroid biochemistry and molecular biology 20041101

Title: Characterization of vitamin D-mediated induction of the CYP 24 transcription.

Journal: Molecular and cellular endocrinology 20041029

Title: Effects of 24,25(OH)2D3, 1,25(OH)2D3 and 25(OH)D3 on alkaline and tartrate-resistant acid phosphatase activities in fetal rat calvaria.

Journal: Journal of physiology and biochemistry 20040901

Title: Fully automated method for the determination of 24,25(OH)2 and 25(OH) D3 hydroxyvitamins, and vitamins A and E in human serum by HPLC.

Journal: Journal of pharmaceutical and biomedical analysis 20040528

Title: Mechanisms regulating differential activation of membrane-mediated signaling by 1alpha,25(OH)2D3 and 24R,25(OH)2D3.

Journal: The Journal of steroid biochemistry and molecular biology 20040501

Title: Novel metabolism of 1 alpha,25-dihydroxyvitamin D3 with C24-C25 bond cleavage catalyzed by human CYP24A1.

Journal: Biochemistry 20040420

Title: C-3 epimerization of vitamin D3 metabolites and further metabolism of C-3 epimers: 25-hydroxyvitamin D3 is metabolized to 3-epi-25-hydroxyvitamin D3 and subsequently metabolized through C-1alpha or C-24 hydroxylation.

Journal: The Journal of biological chemistry 20040416

Title: Osteocalcin fragment in bone matrix enhances osteoclast maturation at a late stage of osteoclast differentiation.

Journal: Journal of bone and mineral metabolism 20040101

Title: Membrane actions of vitamin D metabolites 1alpha,25(OH)2D3 and 24R,25(OH)2D3 are retained in growth plate cartilage cells from vitamin D receptor knockout mice.

Journal: Journal of cellular biochemistry 20031215

Title: Mitochondrial alkaline phosphatase as an intracellular signal in the synthesis of 1,25(OH)2D3 and 24,25(OH)2D3 in LLC-PK1 cells.

Journal: Journal of physiology and biochemistry 20031201

Title: Dietary 135-fold cholecalciferol supplementation severely disturbs the endochondral ossification in growing dogs.

Journal: Domestic animal endocrinology 20030501

Title: Mechanisms for the reduction of 24,25-dihydroxyvitamin D3 levels and bone mass in 24-hydroxylase transgenic rats.

Journal: FASEB journal : official publication of the Federation of American Societies for Experimental Biology 20030401

Title: Environmental salinity regulates receptor expression, cellular effects, and circulating levels of two antagonizing hormones, 1,25-dihydroxyvitamin D3 and 24,25-dihydroxyvitamin D3, in rainbow trout.

Journal: Endocrinology 20030201

Title: Membrane receptors for vitamin D steroid hormones: potential new drug targets.

Journal: Current drug targets 20030101

Title: Steroid hormone action in musculoskeletal cells involves membrane receptor and nuclear receptor mechanisms.

Journal: Connective tissue research 20030101

Title: Update on biological actions of 1alpha,25(OH)2-vitamin D3 (rapid effects) and 24R,25(OH)2-vitamin D3.

Journal: Molecular and cellular endocrinology 20021129

Title: 1alpha,25-dihydroxyvitamin D(3) and 24R,25-dihydroxyvitamin D(3) modulate growth plate chondrocyte physiology via protein kinase C-dependent phosphorylation of extracellular signal-regulated kinase 1/2 mitogen-activated protein kinase.

Journal: Endocrinology 20020701

Title: Deletion of deoxyribonucleic acid binding domain of the vitamin D receptor abrogates genomic and nongenomic functions of vitamin D.

Journal: Molecular endocrinology (Baltimore, Md.) 20020701

Title: Membrane mediated signaling mechanisms are used differentially by metabolites of vitamin D(3) in musculoskeletal cells.

Journal: Steroids 20020501

Title: Dehydroepiandrosterone (DHEA) as a possible source for estrogen formation in bone cells: correlation between bone mineral density and serum DHEA-sulfate concentration in postmenopausal women, and the presence of aromatase to be enhanced by 1,25-dihydroxyvitamin D3 in human osteoblasts.

Journal: Mechanisms of ageing and development 20020430

Title: Evidence for distinct membrane receptors for 1 alpha,25-(OH)(2)D(3) and 24R,25-(OH)(2)D(3) in osteoblasts.

Journal: Steroids 20020301

Title: 1,25-dihydroxyvitamin D3 stimulates vascular endothelial growth factor release in aortic smooth muscle cells: role of p38 mitogen-activated protein kinase.

Journal: Archives of biochemistry and biophysics 20020201

Title: Antagonistic effects of 24R,25-dihydroxyvitamin D3 and 25-hydroxyvitamin D3 on L-type Ca2+ channels and Na+/Ca2+ exchange in enterocytes from Atlantic cod (Gadus morhua).

Journal: Journal of molecular endocrinology 20020201

Title: Rat costochondral chondrocytes produce 17beta-estradiol and regulate its production by 1alpha,25(OH)(2)D(3).

Journal: Bone 20020101

Title: Differential regulation of growth plate chondrocytes by 1alpha,25-(OH)2D3 and 24R,25-(OH)2D3 involves cell-maturation-specific membrane-receptor-activated phospholipid metabolism.

Journal: Critical reviews in oral biology and medicine : an official publication of the American Association of Oral Biologists 20020101

Title: 1,25(OH)2D3-mediated phosphate uptake in isolated chick intestinal cells: effect of 24,25(OH)2D3, signal transduction activators, and age.

Journal: Journal of cellular biochemistry 20020101

Title: The synthesis of [26,27-11C]dihydroxyvitamin D(3), a tracer for positron emission tomography (PET).

Journal: Bioorganic & medicinal chemistry 20011201

Title: 1alpha,25-(OH)2D3 regulates 25-hydroxyvitamin D3 24R-hydroxylase activity in growth zone costochondral growth plate chondrocytes via protein kinase C.

Journal: Calcified tissue international 20011201

Title: Conflicting actions of parathyroid hormone-related protein and serum calcium as regulators of 25-hydroxyvitamin D(3)-1 alpha-hydroxylase expression in a nude rat model of humoral hypercalcemia of malignancy.

Journal: The Journal of endocrinology 20011101

Title: Osteoporosis, bone turnover and hypogonadism in elderly men with treated leprosy.

Journal: Leprosy review 20010901

Title: Putative basal lateral membrane receptors for 24,25-dihydroxyvitamin D(3) in carp and Atlantic cod enterocytes: characterization of binding and effects on intracellular calcium regulation.

Journal: Journal of cellular biochemistry 20010801

Title: Stathmin levels in growth plate chondrocytes are modulated by vitamin D3 metabolites and transforming growth factor-beta1 and are associated with proliferation.

Journal: Endocrine 20010601

Title: The hormonal milieu in early stages of bone cell differentiation modifies the subsequent sex-specific responsiveness of the developing bone to gonadal steroids.

Journal: Journal of bone and mineral research : the official journal of the American Society for Bone and Mineral Research 20010501

Title: Determination of 24,25-dihydroxyvitamin D(3) in human plasma using liquid chromatography-mass spectrometry after derivatization with a Cookson-type reagent.

Journal: Biomedical chromatography : BMC 20010401

Title: Metalloproteinase activity in growth plate chondrocyte cultures is regulated by 1,25-(OH)(2)D(3) and 24,25-(OH)(2)D(3) and mediated through protein kinase C.

Journal: Matrix biology : journal of the International Society for Matrix Biology 20010401

Title: Effect of 1alpha,25-dihydroxyvitamin D3 and 24R,25-dihydroxyvitamin D3 on metalloproteinase activity and cell maturation in growth plate cartilage in vivo.

Journal: Endocrine 20010401

Title: Regulation of the 1b isoform of the plasma membrane calcium pump by 1,25-dihydroxyvitamin D3 in rat osteoblast-like cells.

Journal: Journal of bone and mineral research : the official journal of the American Society for Bone and Mineral Research 20010301

Title: Regulation of phospholipase D (PLD) in growth plate chondrocytes by 24R,25-(OH)2D3 is dependent on cell maturation state (resting zone cells) and is specific to the PLD2 isoform.

Journal: Biochimica et biophysica acta 20010115

Title: 24,25-(OH)(2)D(3) regulates cartilage and bone via autocrine and endocrine mechanisms.

Journal: Steroids 20010101

Title: 24,25-Dihydroxyvitamin D(3) and bone metabolism.

Journal: Steroids 20010101

Title: Possible involvement of vitamin D receptor gene polymorphism in male patients with ossification of spinal ligaments.

Journal: Journal of bone and mineral metabolism 20010101

Title: 24,25-dihydroxyvitamin D3 in combination with 1,25-dihydroxyvitamin D3 ameliorates renal osteodystrophy in rats with chronic renal failure.

Journal: Clinical nephrology 20000501

Title: 24R,25-(OH)(2)D(3) mediates its membrane receptor-dependent effects on protein kinase C and alkaline phosphatase via phospholipase A(2) and cyclooxygenase-1 but not cyclooxygenase-2 in growth plate chondrocytes.

Journal: Journal of cellular physiology 20000301

Title: Effect of vitamin D metabolites on calcitriol degradative enzymes in renal failure.

Journal: Kidney international 19940201

Title: Vitamin D3 compounds regulate human immunodeficiency virus type 1 replication in U937 monoblastoid cells and in monocyte-derived macrophages.

Journal: Journal of leukocyte biology 19930201

Title: Effect of 24,25-dihydroxyvitamin D3 on 1,25-dihydroxyvitamin D3 [1,25-(OH)2D3] metabolism in vitamin D-deficient rats infused with 1,25-(OH)2D3.

Journal: Endocrinology 19890101

Title: 1 alpha-hydroxyvitamin D3 treatment of three patients with 1,25-dihydroxyvitamin D-receptor-defect rickets and alopecia.

Journal: Pediatrics 19870701

Title: 24,25(OH)2D3 enhances the calcemic effect of 1,25(OH)2D3 in PTX rats.

Journal: Proceedings of the Society for Experimental Biology and Medicine. Society for Experimental Biology and Medicine (New York, N.Y.) 19870101

Title: Influence of vitamin D3 metabolites on the production of interleukins 1,2 and 3.

Journal: Immunobiology 19851101

Title: 24,25(OH)2D3 enhances the calcemic effect of 1,25(OH)2D3.

Journal: Proceedings of the Society for Experimental Biology and Medicine. Society for Experimental Biology and Medicine (New York, N.Y.) 19851101

Title: Long-term effects of 1,25-dihydroxy vitamin D3 and 24,25-dihydroxy vitamin D3 in renal osteodystrophy.

Journal: The Quarterly journal of medicine 19820101

Title: 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.

Title: 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.

Title: 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

Title: 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.

Title: 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.

Title: 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.

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Tags:55721-11-4 Molecular Formula|55721-11-4 MDL|55721-11-4 SMILES|55721-11-4 Secalciferol