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C463096-100mg

100mg

Available within 8-12 weeks(?)

$1,454.90

Basic Description

Synonyms	(13Z)-retinal \| 13-Cis retinal \| CHEBI:45487 \| IBP64540CD \| MFCD00009343 \| PD049637 \| 13Z-Retinal \| NCGC00258629-01 \| Cobaltum Sulphuricum \| DTXCID805997 \| cis-Retinal \| DTXSID90143132 \| Retinal, (13Z)- \| 13-cis-Retinal, >=85% (HPLC) \| 13-cis-Retinaldehyd
Specifications & Purity	≥85%(HPLC)
Storage Temp	Store at -20°C
Shipped In	Ice chest + Ice pads

Associated Targets(Human)

ESR1 Tclin Estrogen receptor alpha (17718 Activities)

Discover Target: ESR1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

TSHR Tclin Thyroid stimulating hormone receptor (29986 Activities)

Discover Target: TSHR

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

PPARG Tclin Peroxisome proliferator-activated receptor gamma (15191 Activities)

Discover Target: PPARG

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

KCNH2 Tclin HERG (29587 Activities)

Discover Target: KCNH2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

RXRA Tclin Retinoid X receptor alpha (3637 Activities)

Discover Target: RXRA

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CXCL8 Tchem Interleukin-8 (642 Activities)

Discover Target: CXCL8

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

ALDH1A1 Tchem Aldehyde dehydrogenase 1A1 (77053 Activities)

Discover Target: ALDH1A1

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

NR1H4 Tclin Bile acid receptor FXR (6228 Activities)

Discover Target: NR1H4

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

CYP3A4 Tclin Cytochrome P450 3A4 (53859 Activities)

Discover Target: CYP3A4

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Lymphoblastoid cell (5959 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Associated Targets(non-human)

Cruzipain (33337 Activities)

Explore this target

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

lef Anthrax lethal factor (7585 Activities)

Discover Target: lef

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Nfe2l2 Nuclear factor erythroid 2-related factor 2 (214 Activities)

Discover Target: Nfe2l2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Rorc Nuclear receptor ROR-gamma (89407 Activities)

Discover Target: Rorc

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Nr1i2 Nuclear receptor subfamily 1 group I member 2 (14 Activities)

Discover Target: Nr1i2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mechanisms of Action

Mechanism of Action	Action Type	target ID	Target Name	Target Type	Target Organism	Binding Site Name	References

Names and Identifiers

IUPAC Name	(2Z,4E,6E,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-HWCYFHEPSA-N
Canonical SMILES	CC1=C(C(CCC1)(C)C)C=CC(=CC=CC(=CC=O)C)C
Isomeric SMILES	CC1=C(C(CCC1)(C)C)/C=C/C(=C/C=C/C(=C\C=O)/C)/C
WGK Germany	3
PubChem CID	6436079
Molecular Weight	284.44

Certificates

Certificate of Analysis(COA)

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Safety and Hazards(GHS)

Pictogram(s)	GHS07
Signal	Warning
Hazard Statements	H315:Causes skin irritation H302:Harmful if swallowed H312:Harmful in contact with skin H332:Harmful if inhaled
Precautionary Statements	P261:Avoid breathing dust/fume/gas/mist/vapors/spray. P280:Wear protective gloves/protective clothing/eye protection/face protection. P302+P352:IF ON SKIN: wash with plenty of water. P321:Specific treatment (see ... on this label). P501:Dispose of contents/container to ... P264:Wash hands [and …] thoroughly after handling. P271:Use only outdoors or in a well-ventilated area. P270:Do not eat, drink or smoke when using this product. P304+P340:IF INHALED: Remove person to fresh air and keep comfortable for breathing. P362+P364:Take off contaminated clothing and wash it before reuse. P330:Rinse mouth. P301+P317:IF SWALLOWED: Get medical help. P317:Get emergency medical help. P332+P317:If skin irritation occurs: Get medical help.
WGK Germany	3

References

1. W C Hope,B J Patel,C Fiedler-Nagy,B H Wittreich. (1990-10-01) Retinoids inhibit phospholipase A2 in human synovial fluid and arachidonic acid release from rat peritoneal macrophages.. Inflammation, 14 ((5)): (543-559). [PMID:2123476]
2. M Resnicoff,E E Medrano. (1989-03-01) Growth factors and hormones which affect survival, growth, and differentiation of the MCF-7 stem cells and their descendants.. Experimental cell research, 181 ((1)): (116-125). [PMID:2645148]
3. J Hirayma,N Kamo,Y Imamoto,Y Shichida,T Yoshizawa. (1995-05-08) Reason for the lack of light-dark adaptation in pharaonis phoborhodopsin: reconstitution with 13-cis-retinal.. FEBS letters, 364 ((2)): (168-170). [PMID:7750563]
4. J K McBee,V Kuksa,R Alvarez,A R de Lera,O Prezhdo,F Haeseleer,I Sokal,K Palczewski. (2000-09-14) Isomerization of all-trans-retinol to cis-retinols in bovine retinal pigment epithelial cells: dependence on the specificity of retinoid-binding proteins.. Biochemistry, 39 ((37)): (11370-11380). [PMID:10985782]
5. Amir Aharoni,Michael Ottolenghi,Mordechai Sheves. (2002-04-20) Light-induced hydrolysis and rebinding of nonisomerizable bacteriorhodopsin pigment.. Biophysical journal, 82 ((5)): (2617-2626). [PMID:11964248]
6. Isabelle Gagnon,Gregg Duester,Pangala V Bhat. (2002-05-02) Kinetic analysis of mouse retinal dehydrogenase type-2 (RALDH2) for retinal substrates.. Biochimica et biophysica acta, 1596 ((1)): (156-162). [PMID:11983430]
7. Lioubov I Brueggemann,Jack M Sullivan. (2002-05-30) HEK293S cells have functional retinoid processing machinery.. The Journal of general physiology, 119 ((6)): (593-612). [PMID:12034766]
8. Isabelle Gagnon,Gregg Duester,Pangala V Bhat. (2003-05-20) Enzymatic characterization of recombinant mouse retinal dehydrogenase type 1.. Biochemical pharmacology, 65 ((10)): (1685-1690). [PMID:12754104]
9. Alexandre Santos,Loreley Calvet,Marie-Josee Terrier-Lacombe,Annette Larsen,Jean Bénard,Corinne Pondarré,Geneviève Aubert,Jackie Morizet,François Lavelle,Gilles Vassal. (2004-05-06) In vivo treatment with CPT-11 leads to differentiation of neuroblastoma xenografts and topoisomerase I alterations.. Cancer research, 64 ((9)): (3223-3229). [PMID:15126363]
10. Taichi Nishikawa,Midori Murakami,Tsutomu Kouyama. (2005-08-09) Crystal structure of the 13-cis isomer of bacteriorhodopsin in the dark-adapted state.. Journal of molecular biology, 352 ((2)): (319-328). [PMID:16084526]
11. Valentyn I Prokhorenko,Andrea M Nagy,Stephen A Waschuk,Leonid S Brown,Robert R Birge,R J Dwayne Miller. (2006-09-02) Coherent control of retinal isomerization in bacteriorhodopsin.. Science (New York, N.Y.), 313 ((5791)): (1257-1261). [PMID:16946063]
12. Rosangelly Flores-Perez,Amit K Gupta,Rashid Bashir,Albena Ivanisevic. (2007-05-19) Cantilever-based sensor for the detection of different chromophore isomers.. Analytical chemistry, 79 ((12)): (4702-4708). [PMID:17508721]
13. Masahiro Kono,Rosalie K Crouch. (2011-02-15) Probing human red cone opsin activity with retinal analogues.. Journal of natural products, 74 ((3)): (391-394). [PMID:21314100]
14. Gang Dai,Yu Zhang,Jun Tamogami,Makoto Demura,Naoki Kamo,Hideki Kandori,Tatsuo Iwasa. (2011-07-22) An amino acid residue (S201) in the retinal binding pocket regulates the photoreaction pathway of phoborhodopsin.. Biochemistry, 50 ((33)): (7177-7183). [PMID:21774470]
15. Hye Jin Kim,Jin Zhao,Janet R Sparrow. (2020-09-23) Vitamin A aldehyde-taurine adduct and the visual cycle.. Proceedings of the National Academy of Sciences of the United States of America, 117 ((40)): (24867-24875). [PMID:32958638]
16. C C Huang. (1986-01-01) Effect of retinoids on the growth of squamous cell carcinoma of the palate in rats.. American journal of otolaryngology, 7 ((1)): (55-57). [PMID:3456728]
17. U C Fischer,D Oesterhelt. (1980-07-01) Changes in the protonation state of bacterio-opsin during reconstitution of bacteriorhodopsin.. Biophysical journal, 31 ((1)): (139-145). [PMID:6268211]
18. T Tanaka,Y Urade,H Kimura,N Eguchi,A Nishikawa,O Hayaishi. (1997-06-20) Lipocalin-type prostaglandin D synthase (beta-trace) is a newly recognized type of retinoid transporter.. The Journal of biological chemistry, 272 ((25)): (15789-15795). [PMID:9188476]
19. F Gai,K C Hasson,J C McDonald,P A Anfinrud. (1998-04-16) Chemical dynamics in proteins: the photoisomerization of retinal in bacteriorhodopsin.. Science (New York, N.Y.), 279 ((5358)): (1886-1891). [PMID:9506931]
20. H Stecher,O Prezhdo,J Das,R K Crouch,K Palczewski. (1999-10-16) Isomerization of all-trans-9- and 13-desmethylretinol by retinal pigment epithelial cells.. Biochemistry, 38 ((41)): (13542-13550). [PMID:10521261]
21. De-liang Chen,Guang-yu Wang,Bing Xu,Kun-sheng Hu. (2002-04-19) All-trans to 13-cis retinal isomerization in light-adapted bacteriorhodopsin at acidic pH.. Journal of photochemistry and photobiology. B, Biology, 66 ((3)): (188-194). [PMID:11960728]
22. Sergey L Znoiko,Baerbel Rohrer,Kangmo Lu,Heather R Lohr,Rosalie K Crouch,Jian-Xing Ma. (2005-03-26) Downregulation of cone-specific gene expression and degeneration of cone photoreceptors in the Rpe65-/- mouse at early ages.. Investigative ophthalmology & visual science, 46 ((4)): (1473-1479). [PMID:15790918]
23. Akira Kawanabe,Yuji Furutani,Kwang-Hwan Jung,Hideki Kandori. (2006-04-06) FTIR study of the photoisomerization processes in the 13-cis and all-trans forms of Anabaena sensory rhodopsin at 77 K.. Biochemistry, 45 ((14)): (4362-4370). [PMID:16584171]
24. Majed Chergui. (2006-09-02) Chemistry. Controlling biological functions.. Science (New York, N.Y.), 313 ((5791)): (1246-1247). [PMID:16946057]
25. Oliver Grauer,Christina Pascher,Christian Hartmann,Florian Zeman,Michael Weller,Martin Proescholdt,Alexander Brawanski,Thorsten Pietsch,Wolfgang Wick,Ulrich Bogdahn,Peter Hau. (2011-03-05) Temozolomide and 13-cis retinoic acid in patients with anaplastic gliomas: a prospective single-arm monocentric phase-II study (RNOP-05).. Journal of neuro-oncology, 104 ((3)): (801-809). [PMID:21373969]
26. Amir Wand,Noga Friedman,Mordechai Sheves,Sanford Ruhman. (2012-02-15) Ultrafast photochemistry of light-adapted and dark-adapted bacteriorhodopsin: effects of the initial retinal configuration.. The journal of physical chemistry. B, 116 ((35)): (10444-10452). [PMID:22329764]
27. A Filipowicz,S Wołowiec. (2012-09-14) Bioconjugates of PAMAM dendrimers with trans-retinal, pyridoxal, and pyridoxal phosphate.. International journal of nanomedicine, 7 (4819-4828). [PMID:22973101]

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13-cis-Retinal - ≥85% (HPLC), high purity , CAS No.472-86-6