9-cis-Retinal

Names

[ CAS No. ]:
514-85-2

[ Name ]:
9-cis-Retinal

[Synonym ]:
(2E,4E,6Z,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenal
Retinal, all-trans-
all-trans-Retinene
9-cis-Vitamin A aldehyde
Retinal,9-cis
Isoretinene A
all-trans-retinal
all-trans-Vitamin A aldehyde
9-cis-Retinal
9-C-Retinal
Retinal, (9cis)-
all-trans-retinaldehyde
EINECS 208-188-8
(9cis)-Retinal
9-cis-7,11,13-trans retinal
11-cis-retinal

Biological Activity

[Description]:

9-cis-Retinal is a natural retinoid. Dietary 9-cis-β-carotene generates 9-cis-retinoids via cleavage into 9-cis-retinal. 9-cis Retinal binds to cellular retinol-binding protein-I (CRBP-I) and CRBP-II with Kds of 8 nM and 5 nM, respectively. 9-cis-Retinal expedites differentiation and maturation of rod photoreceptors in retinal organoids[1][2][3].

[Related Catalog]:

Research Areas >> Others

[Target]

Human Endogenous Metabolite

[In Vitro]

The addition of 9-cis-Retinal, instead of the widely used all-trans retinoic acid, accelerates rod photoreceptor differentiation in organoid cultures, with higher rhodopsin expression and more mature mitochondrial morphology evident by day. 9-cis-Retinal can bind opsin to form functioning rhodopsin[3].

[In Vivo]

Treatment with 9-cis-retinal produced a significant recovery of the cone response in interphotoreceptor retinoid-binding protein (IRBP)-/- mice and shows that retinoid deficiency underlies cone dysfunction[4].

[References]

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

[2]. 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.

[3]. 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.

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

Chemical & Physical Properties

[ Density]:
0.9±0.1 g/cm3

[ Boiling Point ]:
421.4±14.0 °C at 760 mmHg

[ Melting Point ]:
56-58ºC(lit.)

[ Molecular Formula ]:
C₂₀H₂₈O

[ Molecular Weight ]:
284.436

[ Flash Point ]:
205.4±12.4 °C

[ Exact Mass ]:
284.214020

[ PSA ]:
17.07000

[ LogP ]:
6.54

[ Vapour Pressure ]:
0.0±1.0 mmHg at 25°C

[ Index of Refraction ]:
1.541

[ Storage condition ]:
-20°C

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: VH6406500

CHEMICAL NAME :: Retinal, 9-cis-

CAS REGISTRY NUMBER :: 514-85-2

BEILSTEIN REFERENCE NO. :: 1914180

LAST UPDATED :: 199701

DATA ITEMS CITED :: 2

MOLECULAR FORMULA :: C20-H28-O

MOLECULAR WEIGHT :: 284.48

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 25 mg/kg

SEX/DURATION :: female 8 day(s) after conception

TOXIC EFFECTS :: Reproductive - Fertility - post-implantation mortality (e.g. dead and/or resorbed implants per total number of implants)

REFERENCE :: TXAPA9 Toxicology and Applied Pharmacology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1959- Volume(issue)/page/year: 83,563,1986

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302-H312-H315-H332

[ Precautionary Statements ]:
P280

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xn

[ Risk Phrases ]:
20/21/22-38

[ RIDADR ]:
NONH for all modes of transport

[ WGK Germany ]:
3

[ RTECS ]:
VH6406500

[ HS Code ]:
2912299000

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2912299000

[ Summary ]:
2912299000. other cyclic aldehydes without other oxygen function. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:5.5%. General tariff:30.0%

Articles

A High-Throughput Drug Screening Strategy for Detecting Rhodopsin P23H Mutant Rescue and Degradation.

Invest. Ophthalmol. Vis. Sci. 56 , 2553-67, (2015)

Inherent instability of the P23H mutant opsin accounts for approximately 10% of autosomal dominant retinitis pigmentosa cases. Our purpose was to develop an overall set of reliable screening strategie...

Cubozoan genome illuminates functional diversification of opsins and photoreceptor evolution.

Sci. Rep. 5 , 11885, (2015)

Animals sense light primarily by an opsin-based photopigment present in a photoreceptor cell. Cnidaria are arguably the most basal phylum containing a well-developed visual system. The evolutionary hi...

Constitutive phospholipid scramblase activity of a G protein-coupled receptor.

Nat. Commun. 5 , 5115, (2014)

Opsin, the rhodopsin apoprotein, was recently shown to be an ATP-independent flippase (or scramblase) that equilibrates phospholipids across photoreceptor disc membranes in mammalian retina, a process...