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127-47-9 | Retinol, acetate
CAS No: 127-47-9 Catalog No: AG000WIV MDL No:MFCD00019413
Product Description
Catalog Number:
AG000WIV
Chemical Name:
Retinol, acetate
CAS Number:
127-47-9
Molecular Formula:
C22H32O2
Molecular Weight:
328.4883
MDL Number:
MFCD00019413
IUPAC Name:
[(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenyl] acetate
InChI:
InChI=1S/C22H32O2/c1-17(9-7-10-18(2)14-16-24-20(4)23)12-13-21-19(3)11-8-15-22(21,5)6/h7,9-10,12-14H,8,11,15-16H2,1-6H3/b10-7+,13-12+,17-9+,18-14+
InChI Key:
QGNJRVVDBSJHIZ-QHLGVNSISA-N
SMILES:
CC(=O)OC/C=C(/C=C/C=C(/C=C/C1=C(C)CCCC1(C)C)\C)\C
UNII:
3LE3D9D6OY
Properties
Complexity:
596
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
4
Exact Mass:
328.24g/mol
Formal Charge:
0
Heavy Atom Count:
24
Hydrogen Bond Acceptor Count:
2
Hydrogen Bond Donor Count:
0
Isotope Atom Count:
0
Molecular Weight:
328.496g/mol
Monoisotopic Mass:
328.24g/mol
Rotatable Bond Count:
7
Topological Polar Surface Area:
26.3A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
6.3
Literature
| Title | Journal |
|---|---|
| Hepatic Detoxification of Bisphenol A is Retinoid-Dependent. | Toxicological sciences : an official journal of the Society of Toxicology 20170501 |
| Retinoids modulate thioacetamide-induced acute hepatotoxicity. | Toxicological sciences : an official journal of the Society of Toxicology 20140601 |
| Lemon (Citrus limon, Burm.f.) essential oil enhances the trans-epidermal release of lipid-(A, E) and water-(B6, C) soluble vitamins from topical emulsions in reconstructed human epidermis. | International journal of cosmetic science 20120801 |
| Nanoscale domains with nematic order in supercooled vitamin-A acetate: molecular dynamics studies. | Physical review. E, Statistical, nonlinear, and soft matter physics 20110501 |
| Retinyl acetate-loaded nanoparticles: dermal penetration and release of the retinyl acetate. | International journal of pharmaceutics 20110214 |
| Retinoid production using metabolically engineered Escherichia coli with a two-phase culture system. | Microbial cell factories 20110101 |
| Development and validation of a dissolution test method for vitamin A in dietary supplement tablets. | Journal of pharmaceutical and biomedical analysis 20101102 |
| Synthesis and SAR studies of 1,4-benzoxazine MenB inhibitors: novel antibacterial agents against Mycobacterium tuberculosis. | Bioorganic & medicinal chemistry letters 20101101 |
| A randomized controlled trial to assess the impact of dietary energy sources, feed supplements, and the presence of super-shedders on the detection of Escherichia coli O157:H7 in feedlot cattle using different diagnostic procedures. | Foodborne pathogens and disease 20100901 |
| An optimized and validated RP-HPLC/UV detection method for simultaneous determination of all-trans-retinol (vitamin A) and alpha-tocopherol (vitamin E) in human serum: comparison of different particulate reversed-phase HPLC columns. | Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20100901 |
| Vitamin A is systemically bioavailable after intratracheal administration with surfactant in an animal model of newborn respiratory distress. | Pediatric research 20100601 |
| Small quantities of carotenoid-rich tropical green leafy vegetables indigenous to Africa maintain vitamin A status in Mongolian gerbils ( Meriones unguiculatus). | The British journal of nutrition 20100601 |
| Chemoprevention of colorectal cancer by targeting APC-deficient cells for apoptosis. | Nature 20100415 |
| Cosmeceuticals: the evidence behind the retinoids. | Aesthetic surgery journal 20100101 |
| Evaluation of potential therapies for a mouse model of human age-related macular degeneration caused by delayed all-trans-retinal clearance. | Investigative ophthalmology & visual science 20091001 |
| Evaluation of 9-cis-retinyl acetate therapy in Rpe65-/- mice. | Investigative ophthalmology & visual science 20090901 |
| Preparation, in vitro and in vivo evaluation of solid-state self-nanoemulsifying drug delivery system (SNEDDS) of vitamin A acetate. | Journal of drug targeting 20090701 |
| Loss of cone photoreceptors caused by chromophore depletion is partially prevented by the artificial chromophore pro-drug, 9-cis-retinyl acetate. | Human molecular genetics 20090615 |
| Involvement of all-trans-retinal in acute light-induced retinopathy of mice. | The Journal of biological chemistry 20090529 |
| Plasma turnover of 3,4-didehydroretinol (vitamin A2) increases in vitamin A-deficient rats fed low versus high dietary fat. | Journal of lipid research 20090401 |
| Application of an allosteric model to describe the interactions among retinol binding protein 4, transthyretin, and small molecule retinol binding protein 4 ligands. | Analytical biochemistry 20090115 |
| Effects of long-term administration of 9-cis-retinyl acetate on visual function in mice. | Investigative ophthalmology & visual science 20090101 |
| Simultaneous determination of benzophenone-3, retinol and retinyl acetate in pig ear skin layers by high-performance liquid chromatography. | Biomedical chromatography : BMC 20081001 |
| New type of microfabricated carbon electrodes for high-performance liquid chromatography--amperometric detection of fat-soluble vitamins and antioxidants. | Journal of chromatography. A 20080711 |
| Simultaneous determination of five fat-soluble vitamins in feed by high-performance liquid chromatography following solid-phase extraction. | Journal of chromatographic science 20080401 |
| [Effect of vitamin A provision on antineoplastic resistance in rats]. | Voprosy pitaniia 20080101 |
| Chemotherapeutic/chemopreventive role of retinoids in chemically induced skin carcinogenesis in albino mice. | International journal of dermatology 20071101 |
| Interactions of human serum albumin with retinoic acid, retinal and retinyl acetate. | Biochemical pharmacology 20070315 |
| Novel retinoid targets in the mouse limb during organogenesis. | Toxicological sciences : an official journal of the Society of Toxicology 20061101 |
| Casting a broad network: fishing for mechanisms of retinoid teratogenicity. | Toxicological sciences : an official journal of the Society of Toxicology 20061101 |
| Simultaneous analysis of Vitamins A and E in infant milk-based formulae by normal-phase high-performance liquid chromatography-diode array detection using a short narrow-bore column. | Journal of chromatography. A 20060728 |
| Alterations in gene expression in rat skin exposed to 56Fe ions and dietary vitamin A acetate. | Radiation research 20060501 |
| Retinoid receptor antagonists alter the pattern of apoptosis in organogenesis stage mouse limbs. | Toxicological sciences : an official journal of the Society of Toxicology 20060301 |
| [Effect of allogenic intracranial transplantation of embryonal neural cell-precursors on the humoral immune response to neurospecific proteins in rabbits]. | Fiziolohichnyi zhurnal (Kiev, Ukraine : 1994) 20060101 |
| Pharmacological and rAAV gene therapy rescue of visual functions in a blind mouse model of Leber congenital amaurosis. | PLoS medicine 20051101 |
| Dietary levels of all-trans retinol affect retinoid nuclear receptor expression and skeletal development in European sea bass larvae. | The British journal of nutrition 20050601 |
| Extra-hepatic vitamin A concentrations in captive Rhesus (Macaca mulatta) and Marmoset (Callithrix jacchus) monkeys fed excess vitamin A. | International journal for vitamin and nutrition research. Internationale Zeitschrift fur Vitamin- und Ernahrungsforschung. Journal international de vitaminologie et de nutrition 20050301 |
| Dehydration reaction of hydroxenin monoacetate in carbon tetrachloride and an aliphatic alcohol under ultrasound irradiation. | Ultrasonics sonochemistry 20050101 |
| The analysis of the zero-order and the second derivative spectra of retinol acetate, tocopherol acetate and coenzyme Q10 and estimation of their analytical usefulness for their simultaneous determination in synthetic mixtures and pharmaceuticals. | Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy 20040801 |
| Transport across liquid membranes containing vitamin A (retinol acetate). | Journal of colloid and interface science 20040315 |
| Tumouricidal activity of gilthead seabream (Sparus aurata L.) natural cytotoxic cells: the role played in vitro and in vivo by retinol acetate. | Fish & shellfish immunology 20030201 |
| [Immunomodulating effect of short-term deep local cooling and its enhancement with vitamin A]. | Patologicheskaia fiziologiia i eksperimental'naia terapiia 20030101 |
| Articular cartilage degradation and de-differentiation of chondrocytes by the systemic administration of retinyl acetate-ectopic production of osteoblast stimulating factor-1 by chondrocytes in mice. | Osteoarthritis and cartilage 20021201 |
| The action of a dietary retinoid on gene expression and cancer induction in electron-irradiated rat skin. | Journal of radiation research 20021201 |
| Changes in some innate defence parameters of seabream (Sparus aurata L.) induced by retinol acetate. | Fish & shellfish immunology 20021001 |
| Dual isotope test for assessing beta-carotene cleavage to vitamin A in humans. | European journal of nutrition 20020801 |
| Production of lipospheres as carriers for bioactive compounds. | Biomaterials 20020601 |
| Increased antibody production by retinoids is related to the fusion partner of human hybridomas. | Bioscience, biotechnology, and biochemistry 20020101 |
| Hydrogen peroxide-induced inhibition of vasomotor activity: evaluation of single and combined treatments with vitamin A and insulin in streptozotocin-diabetic rats. | International journal of experimental diabetes research 20020101 |
| Prevention of neonatal estrogen imprinting by vitamin A as indicated by estrogen receptor expression in the mouse vagina. | Cell and tissue research 20011201 |
| Impaired vitamin A-mediated mucosal IgA response in IL-5 receptor-knockout mice. | Biochemical and biophysical research communications 20010713 |
| Determination of retinoids in human serum, tocopherol and retinyl acetate in pharmaceuticals by RP-LC with electrochemical detection. | Journal of pharmaceutical and biomedical analysis 20010701 |
| The effects of some antioxidant vitamin- and trace element-supplemented diets on activities of SOD, CAT, GSH-Px and LPO levels in chicken tissues. | Cell biochemistry and function 20010601 |
| On-line supercritical fluid extraction/enzymatic hydrolysis of vitamin a esters: a new simplified approach for the determination of vitamins a and e in food. | Journal of agricultural and food chemistry 20010201 |
| Fibroma induction in rat skin following single or multiple doses of 1.0 GeV/nucleon 56Fe ions from the Brookhaven Alternating Gradient Synchrotron (AGS). | Physica medica : PM : an international journal devoted to the applications of physics to medicine and biology : official journal of the Italian Association of Biomedical Physics (AIFB) 20010101 |
| Budd-Chiari syndrome likely related to a slimming drug preparation. | Journal of hepatology 19951101 |
| Co-carcinogenic effect of retinyl acetate on forestomach carcinogenesis of male F344 rats induced with butylated hydroxyanisole. | Japanese journal of cancer research : Gann 19880301 |
| Effects of BHA, d-alpha-tocopherol and retinol acetate on TCDD-mediated changes in lipid peroxidation, glutathione peroxidase activity and survival. | Xenobiotica; the fate of foreign compounds in biological systems 19840701 |
| Virucidal activity of retinal. | Antimicrobial agents and chemotherapy 19790901 |
| Retinyl acetate prophylaxis in cancer of the urinary bladder. | Investigative urology 19790301 |
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