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β-Apo-13-carotenone (D'Orenone) (Synonyms: D'Orenone)

Catalog No.GC33470

β-Apo-13-carotenone (D'Orenone) (D'Orenone) is a naturally occurring β-apocarotenoid functioned as an antagonist of RXRα.

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β-Apo-13-carotenone (D'Orenone) Chemical Structure

Cas No.: 17974-57-1

Size Price Stock Qty
5mg
$360.00
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10mg
$612.00
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25mg
$1,215.00
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50mg
$1,980.00
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100mg
$3,060.00
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Sample solution is provided at 25 µL, 10mM.

Product Documents

Quality Control & SDS

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Protocol

Kinase experiment:

Cos-1 cells are transfected in serum-free medium with three plasmids mixed in the following amounts per well, 0.05 µg of pRL-TK, 2 µg of pRXRE-luciferase, 2.5 µg of pSG5-RXRα in triplicates. Following transfection, the plates are incubated at 37°C in 5 % CO2 for 4 h. The medium is then changed to complete DMEM. Charcoal stripped FBS has been treated with activated carbon to adsorb lipophilic compounds including retinoids. Twenty hours after transfection, cells are treated with test compounds (β-Apo-13-carotenone) that are dissolved in ethanol or 0.1% ethanol alone for an additional 24 h. Cells are washed once with PBS and lysed by incubation with 500 µL passive lysis buffer for 15 min at room temperature. A 20-µL aliquot of cell lysate is then assayed for luciferase activities using a kit[1].

References:

[1]. Eroglu A, et al. The eccentric cleavage product of β-carotene, β-apo-13-carotenone, functions as an antagonist of RXRα. Arch Biochem Biophys. 2010 Dec 1;504(1):11-6.
[2]. Sun J, et al. β-Apo-13-carotenone regulates retinoid X receptor transcriptional activity through tetramerization of the receptor. J Biol Chem. 2014 Nov 28;289(48):33118-24.
[3]. Wang CX, et al. Actions of β-apo-carotenoids in differentiating cells: differential effects in P19 cells and 3T3-L1 adipocytes. Arch Biochem Biophys. 2015 Apr 15;572:2-10.

Background

β-Apo-13-carotenone (D'Orenone) is a naturally occurring β-apocarotenoid functioned as an antagonist of RXRα.

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[1]. 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[2]. 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[3].

[1]. Eroglu A, et al. The eccentric cleavage product of β-carotene, β-apo-13-carotenone, functions as an antagonist of RXRα. Arch Biochem Biophys. 2010 Dec 1;504(1):11-6. [2]. Sun J, et al. β-Apo-13-carotenone regulates retinoid X receptor transcriptional activity through tetramerization of the receptor. J Biol Chem. 2014 Nov 28;289(48):33118-24. [3]. Wang CX, et al. Actions of β-apo-carotenoids in differentiating cells: differential effects in P19 cells and 3T3-L1 adipocytes. Arch Biochem Biophys. 2015 Apr 15;572:2-10.

Chemical Properties

Cas No. 17974-57-1 SDF
Synonyms D'Orenone
Canonical SMILES CC(/C=C/C=C(C)/C=C/C1=C(C)CCCC1(C)C)=O
Formula C18H26O M.Wt 258.4
Solubility DMSO : 33.33 mg/mL (128.99 mM);Water : < 0.1 mg/mL (insoluble) Storage Store at -20°C
General tips Please select the appropriate solvent to prepare the stock solution according to the solubility of the product in different solvents; once the solution is prepared, please store it in separate packages to avoid product failure caused by repeated freezing and thawing.Storage method and period of the stock solution: When stored at -80°C, please use it within 6 months; when stored at -20°C, please use it within 1 month.
To increase solubility, heat the tube to 37°C and then oscillate in an ultrasonic bath for some time.
Shipping Condition Evaluation sample solution: shipped with blue ice. All other sizes available: with RT, or with Blue Ice upon request.

Complete Stock Solution Preparation Table

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1 mg 5 mg 10 mg
1 mM 3.87 mL 19.3498 mL 38.6997 mL
5 mM 0.774 mL 3.87 mL 7.7399 mL
10 mM 0.387 mL 1.935 mL 3.87 mL
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Average Rating: 5 ★★★★★ (Based on Reviews and 3 reference(s) in Google Scholar.)

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