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514-85-2

514-85-2 structure
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: 2025-08-25 17:51:17
  • 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
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
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
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%
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