≥98% for sensitive chromatographic and analytical workflows requiring minimal baseline interference.
Protected from light,Store at -80°C Ships Dry ice packs + Cold packs Check lot-specific COA for exact specifications.
SDS, COA, datasheet, and spec sheet available for download. Lot-specific COA accessible via lot number lookup.
Cited in 0 peer-reviewed publications across chromatography, organic synthesis, and cross-coupling reactions.
β-Apo-13-carotenone (D'Orenone) is a naturally occurring β-apocarotenoid functioned as an antagonist of RXRα .
In Vitro
β-apo-13-Carotenone is identified as enzymatic cleavage products of β-carotene in homogenates of intestinal mucosa of rat. β-apo-13-carotenone is found to antagonize the activation of RXRα by 9-cis-retinoic acid and is effective at concentrations as low as 1nM. Molecular modeling studies reveal that β-apo-13-carotenone makes molecular interactions like an antagonist of RXRα. β-apo-13-carotenone competes for 9cRA binding to RXRα with an affinity (7–8 nM) identical to 9cRA itself. β-apo-13-carotenone antagonizes 9cRA activation of full-length hRXRα with a similar efficiency as the known antagonist UVI3003. β-apo-13-carotenone induces formation of the RXRα transcriptionally silent tetramer but does not inhibit coactivator recruitment to the isolated LBD. The uptake and/or metabolism of β-apo-13-carotenone does not allow for accumulation of these β-carotene metabolites in cells. 3T3-L1 adipocyte marker gene expression is induced by β-apo-carotenoid treatment. MCE has not independently confirmed the accuracy of these methods. They are for reference only.
Form:Oil
| Canonical Smiles | CC1=C(C(CCC1)(C)C)C=CC(=CC=CC(=O)C)C |
|---|---|
| IUPAC Name | (3E,5E,7E)-6-methyl-8-(2,6,6-trimethylcyclohexen-1-yl)octa-3,5,7-trien-2-one |
| InChIKey | UBTNVRPIHJRBCI-LUXGDSJYSA-N |
| INCHI | 1S/C18H26O/c1-14(8-6-10-16(3)19)11-12-17-15(2)9-7-13-18(17,4)5/h6,8,10-12H,7,9,13H2,1-5H3/b10-6+,12-11+,14-8+ |
| Isomeric SMILES | CC1=C(C(CCC1)(C)C)/C=C/C(=C/C=C/C(=O)C)/C |
| PubChem CID | 5363697 |
| MeSH Entry Terms | beta-apo-13-carotenone |
| Molecular Weight | 258.40 |
Comprehensive hazard, handling, storage, and regulatory compliance document.
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View spec sheet →Taxonomy Tree
| Kingdom | Organic compounds |
|---|---|
| Superclass | Lipids and lipid-like molecules |
| Class | Prenol lipids |
| Subclass | Sesquiterpenoids |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Sesquiterpenoids |
| Alternative Parents | Enones Acryloyl compounds Ketones Organic oxides Hydrocarbon derivatives |
| Molecular Framework | Aliphatic homomonocyclic compounds |
| Substituents | Cyclofarsesane sesquiterpenoid - Sesquiterpenoid - Alpha,beta-unsaturated ketone - Enone - Acryloyl-group - Ketone - Organic oxygen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Carbonyl group - Aliphatic homomonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. |
| External Descriptors | enone - apo carotenoid |
| Solubility | DMSO : 110 mg/mL (425.70 mM; Need ultrasonic) |
|---|---|
| Molecular Weight | 258.399 g/mol |
| XLogP3 | 4.800 |
| Hydrogen Bond Donor Count | 0 |
| Hydrogen Bond Acceptor Count | 1 |
| Rotatable Bond Count | 4 |
| Exact Mass | 258.198 Da |
| Monoisotopic Mass | 258.198 Da |
| Topological Polar Surface Area | 17.100 Ų |
| Heavy Atom Count | 19 |
| Formal Charge | 0 |
| Complexity | 456.000 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 3 |
| Undefined Bond Stereocenter Count | 0 |
| The total count of all stereochemical bonds | 3 |
| Covalently-Bonded Unit Count | 1 |
