17592-07-3
17592-07-3
Chemical Structure
Tachysterol 3
- CAS No.: 17592-07-3
- Formula:C27H44O
- Molecular Weight:384.64
IUPAC Name: (S)-4-methyl-3-((E)-2-((1R,3aR,7aR)-7a-methyl-1-((R)-6-methylheptan-2-yl)-2,3,3a,6,7,7a-hexahydro-1H-inden-4-yl)vinyl)cyclohex-3-en-1-ol
InChIKey: YUGCAAVRZWBXEQ-FMCTZRJNSA-N
SMILES: O[C@@H]1CC(/C=C/C2=CCC[C@]3(C)[C@@H]([C@H](C)CCCC(C)C)CC[C@@]23[H])=C(C)CC1
Biological Activity: Tachysterol 3 is a photoproduct of Previtamin D3 (HY-130705). Previtamin D3 is an orally active, thermolabile steroidal compound that generates vitamin D3, as well as biologically inactive lumisterol and tachysterol. Previtamin D3 is synthesized in the skin of humans and rats via the UV-B-mediated photoconversion of 7-dehydrocholesterol. Previtamin D3 lacks direct anti-rachitic activity, and its in vivo activity relies on the vitamin D3 it produces. Previtamin D3 can be used in studies related to rickets and vitamin D metabolism[1][2].
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Tachysterol 3 | Tachysterol 3 is a photoproduct of Previtamin D3 (HY-130705). Previtamin D3 is an orally active, thermolabile steroidal compound that generates vitamin D3, as well as biologically inactive lumisterol and tachysterol. Previtamin D3 is synthesized in the skin of humans and rats via the UV-B-mediated photoconversion of 7-dehydrocholesterol. Previtamin D3 lacks direct anti-rachitic activity, and its in vivo activity relies on the vitamin D3 it produces. Previtamin D3 can be used in studies related to rickets and vitamin D metabolism. | |||||||||||||||||||||
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Isotachysterol 3 | Isotachysterol 3 is an analog of 1,25-dihydrox Vitamin D3. Isotachysterol 3 stimulates intestinal calcium transport and bone calcium mobilization in anephric rats. | |||||||||||||||||||||
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Previtamin D3 | Previtamin D3 is an orally active, thermolabile steroidal compound that generates vitamin D3, as well as biologically inactive lumisterol and tachysterol. Previtamin D3 is synthesized in the skin of humans and rats via the UV-B-mediated photoconversion of 7-dehydrocholesterol. Previtamin D3 lacks direct anti-rachitic activity, and its in vivo activity relies on the vitamin D3 it produces. Previtamin D3 can be used in studies related to rickets and vitamin D metabolism. | |||||||||||||||||||||
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1α,25-Dihydroxyprevitamin D3 | 1α,25-Dihydroxyprevitamin D3 is the precursor of Vitamin D3. | |||||||||||||||||||||
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(E)-1α,25-Dihydroxyprevitamin D3 | (E)-1α,25-Dihydroxyprevitamin D3 is a structurally related analog of 1α,25(OH)2D3. | |||||||||||||||||||||
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5,6-trans-Vitamin D3 (Standard) | ≥98% | 5,6-trans-Vitamin D3 (Standard) is the analytical standard of 5,6-trans-Vitamin D3. This product is intended for research and analytical applications. 5,6-trans-Vitamin D3 (5,6-trans-Cholecalciferol;5,6-trans-Colecalciferol) is a photoproduct of vitamin D3. Vitamin D3 is a naturally occuring form of vitamin D. Vitamin D3 induces cell differentiation and prevents proliferation of cancer cells. | ||||||||||||||||||||
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3-epi-Vitamin D3 | 94.11% | 3-epi-Vitamin D3 (Epicholecalciferol) (Compound 4), a Vitamin D3 analogue, is a Hedgehog pathway inhibitor with an IC50 of 39.2 μM measured in U87MG cells. | ||||||||||||||||||||
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Vitamin D3-13C5 | Vitamin D3-13C5 is the 13C-labeled Vitamin D3 (HY-15398). Vitamin D3 (Cholecalciferol) is a naturally occuring form of vitamin D. Vitamin D3 induces cell differentiation and prevents proliferation of cancer cells. | |||||||||||||||||||||
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25-Hydroxytachysterol3 | 98.07% | 25-Hydroxytachysterol3 is the metabolite of Vitamin D3 (HY-15398). 25-Hydroxytachysterol3 inhibits the proliferation of epidermal keratinocytes and dermal fibroblasts, stimulates the expression of differentiation- and antioxidant-related genes in keratinocytes. 25-Hydroxytachysterol3 activates vitamin D receptor (VDR) and aryl hydrocarbon receptor (AhR), liver X receptor α/β (LXR α/β) and peroxisome proliferator-activated receptor γ (PPARγ), stimulates the expression of CYP24A1. | ||||||||||||||||||||
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Previtamin D2 | Previtamin D2 is a precursor to Vitamin D2 (ergocalciferol) , formed through the photoisomerization of ergosterol, a compound found in fungi and some plants. Exposure to ultraviolet (UV) light triggers the conversion of ergosterol to previtamin D2, which then rapidly isomerizes to vitamin D2. | |||||||||||||||||||||
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1α,25-Dihydroxyprevitamin D3 impurity 1 | 1α,25-Dihydroxyprevitamin D3 impurity 1 is an impurity of 1α,25-Dihydroxyprevitamin D3 (HY-131450). | |||||||||||||||||||||
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References
- [1]. Cecilia Cisneros, et al. The Role of Tachysterol in Vitamin D Photosynthesis - A Non-Adiabatic Molecular Dynamics Study. Phys Chem Chem Phys. 2017 Feb 22;19(8):5763-5777. [Content Brief]
- [2]. Slominski AT, et al. Metabolic activation of tachysterol3 to biologically active hydroxyderivatives that act on VDR, AhR, LXRs, and PPARγ receptors. FASEB J. 2022 Aug;36(8):e22451. [Content Brief]
