Home Other Building Blocks 514-85-2
514-85-2,MFCD00135842
Catalog No.:AA00DDGA

514-85-2 | 9-CIS-RETINAL

Pack Size
Purity
Availability
Price(USD)
Quantity
  
1mg
≥98%
in stock  
$70.00   $49.00
- +
5mg
≥98%
in stock  
$289.00   $202.00
- +
10mg
≥98%
in stock  
$376.00   $263.00
- +
  • Technical Information
  • Properties
  • Literature
  • Request for Quotation
  • Download SDS
  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA00DDGA
Chemical Name:
9-CIS-RETINAL
CAS Number:
514-85-2
Molecular Formula:
C20H28O
Molecular Weight:
284.4357
MDL Number:
MFCD00135842
SMILES:
O=C/C=C(/C=C/C=C(\C=C\C1=C(C)CCCC1(C)C)/C)\C
Properties
Properties
 
Form:
Solid  
MP:
61-63°C  
Storage:
Keep in dry area;-20 ℃;  

Computed Properties
 
Complexity:
522  
Covalently-Bonded Unit Count:
1  
Defined Bond Stereocenter Count:
4  
Heavy Atom Count:
21  
Hydrogen Bond Acceptor Count:
1  
Rotatable Bond Count:
5  
XLogP3:
6.2  

Literature

Title: 9-cis retinoic acid is the ALDH1A1 product that stimulates melanogenesis.

Journal: Experimental dermatology 20130301

Title: A microparticle/hydrogel combination drug-delivery system for sustained release of retinoids.

Journal: Investigative ophthalmology & visual science 20120901

Title: Melanopsin is highly resistant to light and chemical bleaching in vivo.

Journal: The Journal of biological chemistry 20120615

Title: Light-sensitive coupling of rhodopsin and melanopsin to G(i/o) and G(q) signal transduction in Caenorhabditis elegans.

Journal: FASEB journal : official publication of the Federation of American Societies for Experimental Biology 20120201

Title: M-opsin protein degradation is inhibited by MG-132 in Rpe65⁻/⁻ retinal explant culture.

Journal: Molecular vision 20120101

Title: Retinaldehyde is a substrate for human aldo-keto reductases of the 1C subfamily.

Journal: The Biochemical journal 20111215

Title: Molecular mechanisms of disease for mutations at Gly-90 in rhodopsin.

Journal: The Journal of biological chemistry 20111118

Title: CrbpI modulates glucose homeostasis and pancreas 9-cis-retinoic acid concentrations.

Journal: Molecular and cellular biology 20110801

Title: Binding affinities of CRBPI and CRBPII for 9-cis-retinoids.

Journal: Biochimica et biophysica acta 20110501

Title: 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: Journal of natural products 20110325

Title: Effective and sustained delivery of hydrophobic retinoids to photoreceptors.

Journal: Investigative ophthalmology & visual science 20101101

Title: Improvement of visual performance with intravitreal administration of 9-cis-retinal in Rpe65-mutant dogs.

Journal: Archives of ophthalmology (Chicago, Ill. : 1960) 20101101

Title: Blind dogs that can see: pharmacological treatment of Leber congenital amaurosis caused by a defective visual cycle.

Journal: Archives of ophthalmology (Chicago, Ill. : 1960) 20101101

Title: Retinobenzaldehydes as proper-trafficking inducers of folding-defective P23H rhodopsin mutant responsible for retinitis pigmentosa.

Journal: Bioorganic & medicinal chemistry 20101001

Title: Nonadiabatic ab initio dynamics of a model protonated Schiff base of 9-cis retinal.

Journal: The journal of physical chemistry. A 20100819

Title: Retinoids activate RXR/CAR-mediated pathway and induce CYP3A.

Journal: Biochemical pharmacology 20100115

Title: Release of 11-cis-retinal from cellular retinaldehyde-binding protein by acidic lipids.

Journal: Molecular vision 20090101

Title: Reprogramming progeny cells of embryonic RPE to produce photoreceptors: development of advanced photoreceptor traits under the induction of neuroD.

Journal: Investigative ophthalmology & visual science 20080901

Title: Structural basis for the high all-trans-retinaldehyde reductase activity of the tumor marker AKR1B10.

Journal: Proceedings of the National Academy of Sciences of the United States of America 20071226

Title: Characterization of an oligomeric carbonyl reductase of dog liver: its identity with peroxisomal tetrameric carbonyl reductase.

Journal: Biological & pharmaceutical bulletin 20070901

Title: Cantilever-based sensor for the detection of different chromophore isomers.

Journal: Analytical chemistry 20070615

Title: Ontogeny of rdh9 (Crad3) expression: ablation causes changes in retinoid and steroid metabolizing enzymes, but RXR and androgen signaling seem normal.

Journal: Biochimica et biophysica acta 20070401

Title: Alcohol dehydrogenase 2 is a major hepatic enzyme for human retinol metabolism.

Journal: Cellular and molecular life sciences : CMLS 20070201

Title: Light induces programmed cell death by activating multiple independent proteases in a cone photoreceptor cell line.

Journal: Investigative ophthalmology & visual science 20070101

Title: Improvement in rod and cone function in mouse model of Fundus albipunctatus after pharmacologic treatment with 9-cis-retinal.

Journal: Investigative ophthalmology & visual science 20061001

Title: Kinetic properties of chimeric class I aldehyde dehydrogenases for retinal isomers.

Journal: Biochemistry and cell biology = Biochimie et biologie cellulaire 20061001

Title: Retinoids activate the RXR/SXR-mediated pathway and induce the endogenous CYP3A4 activity in Huh7 human hepatoma cells.

Journal: Toxicological sciences : an official journal of the Society of Toxicology 20060701

Title: 9-cis Retinal increased in retina of RPE65 knockout mice with decrease in coat pigmentation.

Journal: Photochemistry and photobiology 20060101

Title: Opsin activation of transduction in the rods of dark-reared Rpe65 knockout mice.

Journal: The Journal of physiology 20051001

Title: Intrinsically photosensitive retinal ganglion cells detect light with a vitamin A-based photopigment, melanopsin.

Journal: Proceedings of the National Academy of Sciences of the United States of America 20050719

Title: Breaking the covalent bond--a pigment property that contributes to desensitization in cones.

Journal: Neuron 20050616

Title: Vitamin a deficiency in patients with common variable immunodeficiency.

Journal: Journal of clinical immunology 20050501

Title: Downregulation of cone-specific gene expression and degeneration of cone photoreceptors in the Rpe65-/- mouse at early ages.

Journal: Investigative ophthalmology & visual science 20050401

Title: Cis-retinol dehydrogenase: 9-cis-retinol metabolism and its effect on proliferation of human MCF7 breast cancer cells.

Journal: Experimental cell research 20050201

Title: Impairment of the transient pupillary light reflex in Rpe65(-/-) mice and humans with leber congenital amaurosis.

Journal: Investigative ophthalmology & visual science 20040401

Title: Enzymatic characterization of recombinant mouse retinal dehydrogenase type 1.

Journal: Biochemical pharmacology 20030515

Title: Cloning of monkey RALDH1 and characterization of retinoid metabolism in monkey kidney proximal tubule cells.

Journal: Journal of lipid research 20030201

Title: The cellular fate of mutant rhodopsin: quality control, degradation and aggresome formation.

Journal: Journal of cell science 20020715

Title: Recovery of visual functions in a mouse model of Leber congenital amaurosis.

Journal: The Journal of biological chemistry 20020524

Title: Recombinant class I aldehyde dehydrogenases specific for all-trans- or 9-cis-retinal.

Journal: The Journal of biological chemistry 20020517

Title: Kinetic analysis of mouse retinal dehydrogenase type-2 (RALDH2) for retinal substrates.

Journal: Biochimica et biophysica acta 20020401

Title: Structural and functional characterization of recombinant human cellular retinaldehyde-binding protein.

Journal: Protein science : a publication of the Protein Society 19980301

Title: Active site-directed inactivation of constitutively active mutants of rhodopsin.

Journal: The Journal of biological chemistry 19940304

Title: Kane MA, et al. Binding affinities of CRBPI and CRBPII for 9-cis-retinoids.Biochim Biophys Acta. 2011 May;1810(5):514-8.

Title: Mertz JR, et al. Identification and characterization of a stereospecific human enzyme that catalyzes 9-cis-retinol oxidation. A possible role in 9-cis-retinoic acid formation. J Biol Chem. 1997 May 2;272(18):11744-9.

Title: Kaya KD, et al. Transcriptome-based molecular staging of human stem cell-derived retinal organoids uncovers accelerated photoreceptor differentiation by 9-cis retinal. Mol Vis. 2019 Nov 11;25:663-678.

Title: Parker RO, et al. Normal cone function requires the interphotoreceptor retinoid binding protein. J Neurosci. 2009 Apr 8;29(14):4616-21.

Quotation Request
Company Name:
*
Contact Person:
*
Email:
*
Quantity Required:
*
Country:
Additional Info:
SDS
Tags:514-85-2 Molecular Formula|514-85-2 MDL|514-85-2 SMILES|514-85-2 9-CIS-RETINAL