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9-CIS-RETINAL

CAS No.:
514-85-2
Catalog Number:
AG00DDJ2
Molecular Formula:
C20H28O
Molecular Weight:
284.4357
Pack Size
Purity
Availability
Location
Price(USD)
Quantity
  
1mg
≥98%
1 week
United States
$111
- +
5mg
≥98%
1 week
United States
$287
- +
10mg
≥98%
1 week
United States
$355
- +
Product Description
Catalog Number:
AG00DDJ2
Chemical Name:
9-CIS-RETINAL
CAS Number:
514-85-2
Molecular Formula:
C20H28O
Molecular Weight:
284.4357
MDL Number:
MFCD00135842
IUPAC Name:
(2E,4E,6Z,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenal
InChI:
InChI=1S/C20H28O/c1-16(8-6-9-17(2)13-15-21)11-12-19-18(3)10-7-14-20(19,4)5/h6,8-9,11-13,15H,7,10,14H2,1-5H3/b9-6+,12-11+,16-8-,17-13+
InChI Key:
NCYCYZXNIZJOKI-MKOSUFFBSA-N
SMILES:
O=C/C=C(/C=C/C=C(\C=C\C1=C(C)CCCC1(C)C)/C)\C
EC Number:
208-188-8
Properties
Complexity:
522  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
0
Defined Bond Stereocenter Count:
4  
Exact Mass:
284.214g/mol
Formal Charge:
0
Heavy Atom Count:
21  
Hydrogen Bond Acceptor Count:
1  
Hydrogen Bond Donor Count:
0
Isotope Atom Count:
0
Molecular Weight:
284.443g/mol
Monoisotopic Mass:
284.214g/mol
Rotatable Bond Count:
5  
Topological Polar Surface Area:
17.1A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
6.2  
Literature
Title Journal
9-cis retinoic acid is the ALDH1A1 product that stimulates melanogenesis. Experimental dermatology 20130301
A microparticle/hydrogel combination drug-delivery system for sustained release of retinoids. Investigative ophthalmology & visual science 20120901
Melanopsin is highly resistant to light and chemical bleaching in vivo. The Journal of biological chemistry 20120615
Light-sensitive coupling of rhodopsin and melanopsin to G(i/o) and G(q) signal transduction in Caenorhabditis elegans. FASEB journal : official publication of the Federation of American Societies for Experimental Biology 20120201
M-opsin protein degradation is inhibited by MG-132 in Rpe65⁻/⁻ retinal explant culture. Molecular vision 20120101
Retinaldehyde is a substrate for human aldo-keto reductases of the 1C subfamily. The Biochemical journal 20111215
Molecular mechanisms of disease for mutations at Gly-90 in rhodopsin. The Journal of biological chemistry 20111118
CrbpI modulates glucose homeostasis and pancreas 9-cis-retinoic acid concentrations. Molecular and cellular biology 20110801
Binding affinities of CRBPI and CRBPII for 9-cis-retinoids. Biochimica et biophysica acta 20110501
Cyclopropyl and isopropyl derivatives of 11-cis and 9-cis retinals at C-9 and C-13: subtle steric differences with major effects on ligand efficacy in rhodopsin. Journal of natural products 20110325
Effective and sustained delivery of hydrophobic retinoids to photoreceptors. Investigative ophthalmology & visual science 20101101
Improvement of visual performance with intravitreal administration of 9-cis-retinal in Rpe65-mutant dogs. Archives of ophthalmology (Chicago, Ill. : 1960) 20101101
Blind dogs that can see: pharmacological treatment of Leber congenital amaurosis caused by a defective visual cycle. Archives of ophthalmology (Chicago, Ill. : 1960) 20101101
Retinobenzaldehydes as proper-trafficking inducers of folding-defective P23H rhodopsin mutant responsible for retinitis pigmentosa. Bioorganic & medicinal chemistry 20101001
Nonadiabatic ab initio dynamics of a model protonated Schiff base of 9-cis retinal. The journal of physical chemistry. A 20100819
Retinoids activate RXR/CAR-mediated pathway and induce CYP3A. Biochemical pharmacology 20100115
Release of 11-cis-retinal from cellular retinaldehyde-binding protein by acidic lipids. Molecular vision 20090101
Reprogramming progeny cells of embryonic RPE to produce photoreceptors: development of advanced photoreceptor traits under the induction of neuroD. Investigative ophthalmology & visual science 20080901
Structural basis for the high all-trans-retinaldehyde reductase activity of the tumor marker AKR1B10. Proceedings of the National Academy of Sciences of the United States of America 20071226
Characterization of an oligomeric carbonyl reductase of dog liver: its identity with peroxisomal tetrameric carbonyl reductase. Biological & pharmaceutical bulletin 20070901
Cantilever-based sensor for the detection of different chromophore isomers. Analytical chemistry 20070615
Ontogeny of rdh9 (Crad3) expression: ablation causes changes in retinoid and steroid metabolizing enzymes, but RXR and androgen signaling seem normal. Biochimica et biophysica acta 20070401
Alcohol dehydrogenase 2 is a major hepatic enzyme for human retinol metabolism. Cellular and molecular life sciences : CMLS 20070201
Light induces programmed cell death by activating multiple independent proteases in a cone photoreceptor cell line. Investigative ophthalmology & visual science 20070101
Improvement in rod and cone function in mouse model of Fundus albipunctatus after pharmacologic treatment with 9-cis-retinal. Investigative ophthalmology & visual science 20061001
Kinetic properties of chimeric class I aldehyde dehydrogenases for retinal isomers. Biochemistry and cell biology = Biochimie et biologie cellulaire 20061001
Retinoids activate the RXR/SXR-mediated pathway and induce the endogenous CYP3A4 activity in Huh7 human hepatoma cells. Toxicological sciences : an official journal of the Society of Toxicology 20060701
9-cis Retinal increased in retina of RPE65 knockout mice with decrease in coat pigmentation. Photochemistry and photobiology 20060101
Opsin activation of transduction in the rods of dark-reared Rpe65 knockout mice. The Journal of physiology 20051001
Intrinsically photosensitive retinal ganglion cells detect light with a vitamin A-based photopigment, melanopsin. Proceedings of the National Academy of Sciences of the United States of America 20050719
Breaking the covalent bond--a pigment property that contributes to desensitization in cones. Neuron 20050616
Vitamin a deficiency in patients with common variable immunodeficiency. Journal of clinical immunology 20050501
Downregulation of cone-specific gene expression and degeneration of cone photoreceptors in the Rpe65-/- mouse at early ages. Investigative ophthalmology & visual science 20050401
Cis-retinol dehydrogenase: 9-cis-retinol metabolism and its effect on proliferation of human MCF7 breast cancer cells. Experimental cell research 20050201
Impairment of the transient pupillary light reflex in Rpe65(-/-) mice and humans with leber congenital amaurosis. Investigative ophthalmology & visual science 20040401
Enzymatic characterization of recombinant mouse retinal dehydrogenase type 1. Biochemical pharmacology 20030515
Cloning of monkey RALDH1 and characterization of retinoid metabolism in monkey kidney proximal tubule cells. Journal of lipid research 20030201
The cellular fate of mutant rhodopsin: quality control, degradation and aggresome formation. Journal of cell science 20020715
Recovery of visual functions in a mouse model of Leber congenital amaurosis. The Journal of biological chemistry 20020524
Recombinant class I aldehyde dehydrogenases specific for all-trans- or 9-cis-retinal. The Journal of biological chemistry 20020517
Kinetic analysis of mouse retinal dehydrogenase type-2 (RALDH2) for retinal substrates. Biochimica et biophysica acta 20020401
Structural and functional characterization of recombinant human cellular retinaldehyde-binding protein. Protein science : a publication of the Protein Society 19980301
Active site-directed inactivation of constitutively active mutants of rhodopsin. The Journal of biological chemistry 19940304
Properties