514-85-2

514-85-2 structure

Name: 9-cis-Retinal
Chemical Name: 9-cis-retinal
CAS Number: 514-85-2
Molecular Formula: C₂₀H₂₈O
Molecular Weight: 284.436
Catalog: Research Areas Others
Create Date: 2018-04-27 08:00:00
Modify Date: 2024-01-05 17:49:49
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].

Name	9-cis-retinal
Synonyms	(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

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.

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

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

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

Precursor 9
116-31-4 68-26-8 58526-50-4 54340-95-3
145572-38-9 564-87-4 127-47-9 25529-00-4
36678-63-4
DownStream 4
472-86-6 116-31-4 564-87-4 68-26-8

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%

514-85-2	23790-80-9
564-87-4	66901-09-5
29706-61-4	6901-92-4
113085-04-4	13312-52-2
58526-50-4	1431303-55-7