Home >> Research Area >> Apo-12'-Lycopenal

Apo-12'-Lycopenal

CAS# 1071-52-9

Apo-12'-Lycopenal

Catalog No. BCC8298----Order now to get a substantial discount!

Product Name & Size Price Stock
Apo-12'-Lycopenal: 5mg Please Inquire In Stock
Apo-12'-Lycopenal: 10mg Please Inquire In Stock
Apo-12'-Lycopenal: 20mg Please Inquire Please Inquire
Apo-12'-Lycopenal: 50mg Please Inquire Please Inquire
Apo-12'-Lycopenal: 100mg Please Inquire Please Inquire
Apo-12'-Lycopenal: 200mg Please Inquire Please Inquire
Apo-12'-Lycopenal: 500mg Please Inquire Please Inquire
Apo-12'-Lycopenal: 1000mg Please Inquire Please Inquire

Quality Control of Apo-12'-Lycopenal

Number of papers citing our products

Chemical structure

Apo-12'-Lycopenal

3D structure

Chemical Properties of Apo-12'-Lycopenal

Cas No. 1071-52-9 SDF Download SDF
PubChem ID 10904256 Appearance Powder
Formula C25H34O M.Wt 350.5
Type of Compound N/A Storage Desiccate at -20°C
Solubility Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.
Chemical Name (2E,4E,6E,8E,10E,12E,14E)-2,7,11,15,19-pentamethylicosa-2,4,6,8,10,12,14,18-octaenal
SMILES CC(=CCCC(=CC=CC(=CC=CC(=CC=CC=C(C)C=O)C)C)C)C
Standard InChIKey CTKROHWZDNWNMY-MSWJQUEKSA-N
Standard InChI InChI=1S/C25H34O/c1-21(2)12-9-15-23(4)17-11-19-24(5)18-10-16-22(3)13-7-8-14-25(6)20-26/h7-8,10-14,16-20H,9,15H2,1-6H3/b8-7+,16-10+,19-11+,22-13+,23-17+,24-18+,25-14+
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Apo-12'-Lycopenal Dilution Calculator

Concentration (start)
x
Volume (start)
=
Concentration (final)
x
Volume (final)
 
 
 
C1
V1
C2
V2

calculate

Apo-12'-Lycopenal Molarity Calculator

Mass
=
Concentration
x
Volume
x
MW*
 
 
 
g/mol

calculate

Preparing Stock Solutions of Apo-12'-Lycopenal

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.8531 mL 14.2653 mL 28.5307 mL 57.0613 mL 71.3267 mL
5 mM 0.5706 mL 2.8531 mL 5.7061 mL 11.4123 mL 14.2653 mL
10 mM 0.2853 mL 1.4265 mL 2.8531 mL 5.7061 mL 7.1327 mL
50 mM 0.0571 mL 0.2853 mL 0.5706 mL 1.1412 mL 1.4265 mL
100 mM 0.0285 mL 0.1427 mL 0.2853 mL 0.5706 mL 0.7133 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

Organizitions Citing Our Products recently

 
 
 

Calcutta University

University of Minnesota

University of Maryland School of Medicine

University of Illinois at Chicago

The Ohio State University

University of Zurich

Harvard University

Colorado State University

Auburn University

Yale University

Worcester Polytechnic Institute

Washington State University

Stanford University

University of Leipzig

Universidade da Beira Interior

The Institute of Cancer Research

Heidelberg University

University of Amsterdam

University of Auckland
TsingHua University
TsingHua University
The University of Michigan
The University of Michigan
Miami University
Miami University
DRURY University
DRURY University
Jilin University
Jilin University
Fudan University
Fudan University
Wuhan University
Wuhan University
Sun Yat-sen University
Sun Yat-sen University
Universite de Paris
Universite de Paris
Deemed University
Deemed University
Auckland University
Auckland University
The University of Tokyo
The University of Tokyo
Korea University
Korea University
Featured Products
New Products
 

References on Apo-12'-Lycopenal

Apo-12'-lycopenal, a Lycopene Metabolite, Promotes Adipocyte Differentiation via Peroxisome Proliferator-activated Receptor Gamma Activation.[Pubmed:30449105]

J Agric Food Chem. 2018 Nov 19.

Apo-lycopenals, lycopene metabolites produced by an initial cleavage by beta,beta-carotene-9',10'-oxygenase, exhibit diverse biologically active effects. In this study, we investigated the effect of apo-lycopenals on the activation of nuclear receptors involved in glucose and lipid metabolism. Only apo-12'-lycopenal exhibited selective and dose-dependent transactivation activity for peroxisome proliferator-activated receptor gamma (PPARgamma), whereas neither apo-6'- nor 8'-lycopenals displayed this activity (7.83 +/- 0.66-, 1.32 +/- 0.10-, 1.31 +/- 0.37-fold higher activity relative to control, respectively). Additionally, apo-12'-lycopenal promoted adipocyte differentiation of 3T3-L1 cells and subsequently increased the mRNA levels of PPARgamma (a 2.36 +/- 0.07-fold increase relative to control; p < 0.01) and its target genes, as well as enhanced adiponectin secretion (a 3.25 +/- 0.27-fold increase relative to control; p < 0.01) and insulin-stimulated glucose uptake (1486 +/- 85 pmol/well; p < 0.001) in 3T3-L1 cells. Our results indicated that apo-12'-lycopenal promoted adipocyte differentiation by direct binding and activation of PPARgamma.

beta-Carotene-9',10'-oxygenase status modulates the impact of dietary tomato and lycopene on hepatic nuclear receptor-, stress-, and metabolism-related gene expression in mice.[Pubmed:24553694]

J Nutr. 2014 Apr;144(4):431-9.

Tomato and lycopene (psi,psi-carotene) consumption is hypothesized to protect against nonalcoholic steatohepatitis and hepatocarcinogenesis, processes that may depend upon diet and gene interactions. To investigate the interaction of tomato or lycopene feeding with beta-carotene-9',10'-monooxygenase (Bco2) on hepatic metabolic and signaling pathways, male wild-type (WT) and Bco2(-/-) mice (3-wk-old; n = 36) were fed semi-purified control, 10% tomato powder-containing, or 0.25% lycopene beadlet-containing diets for 3 wk. Serum lycopene concentrations were higher in lycopene- and tomato-fed Bco2(-/-) mice compared with WT (P = 0.03). Tomato- and lycopene-fed mice had detectable hepatic apolipoprotein (apo)-6'-, apo-8'-, and apo-12'-lycopenal concentrations. Hepatic expression of beta-carotene-15,15'-monooxygenase was increased in Bco2(-/-) mice compared with WT (P = 0.02), but not affected by diet. Evaluation of hepatic gene expression by focused quantitative reverse transcriptase-polymerase chain reaction arrays for nuclear receptors and coregulators (84 genes) and stress and metabolism (82 genes) genes indicates that tomato feeding affected 31 genes (>/=1.5-fold, P < 0.05) and lycopene feeding affected 19 genes, 16 of which were affected by both diets. Lycopene down-regulation of 7 nuclear receptors and coregulators, estrogen-related receptor-alpha, histone deacetylase 3, nuclear receptor coactivator 4, RevErbA-beta, glucocorticoid receptor, peroxisome proliferator-activated receptor (PPAR)-alpha, and PPAR-gamma, coactivator 1 beta was dependent upon interaction with Bco2 status. Lycopene and tomato feeding induced gene expression patterns consistent with decreased lipid uptake, decreased cell proliferation and mitosis, down-regulated aryl hydrocarbon receptor signaling, and decreased expression of genes involved in retinoid X receptor heterodimer activation. Tomato feeding also caused expression changes consistent with down-regulation of DNA synthesis and terpenoid metabolism. These data suggest tomato components, particularly lycopene, affect hepatic gene expression, potentially affecting hepatic responses to metabolic, infectious, or chemical stress.

Antimetastatic effects and mechanisms of apo-8'-lycopenal, an enzymatic metabolite of lycopene, against human hepatocarcinoma SK-Hep-1 cells.[Pubmed:22211877]

Nutr Cancer. 2012;64(2):274-85.

Lycopene is primarily metabolized by carotenoid monoxygenase II into apo-8'- and apo-12'-lycopenal in the rat liver. Although lycopene possesses antimetastatic activity in a highly invasive hepatoma SK-Hep-1 cell line, little is known whether its metabolites have a similar effect. In this study, we investigated the antimetastatic effects of apo-8'-lycopenal (1-10 muM) in comparison with lycopene (10 muM) in SK-Hep-1 cells. We found that both apo-8'-lycopenal and lycopene inhibited the invasion and migration of SK-Hep-1 cells, and the effect of apo-8'-lycopenal was stronger than that of lycopene at the same concentration (10 muM). Mechanistically, apo-8'-lycopenal: 1) decreased the activities and protein expression of metalloproteinase-2 (MMP-2) and -9; 2) increased the protein expression of nm23-H1 and the tissue inhibitor of MMP (TIMP)-1 and -2; 3) suppressed protein expression of Rho small GTPases; and 4) inhibited focal adhesion kinase-mediated signaling pathway, such as ERK/p38 and PI3K-Akt axis. Overall, these results demonstrate that apo-8'-lycopenal possesses antimetastatic activity in SK-Hep-1 cells and that this effect is stronger than that of lycopene, suggesting that the antimetastatic effect may be attributed, at least in part, to its metabolites such as apo-8'-lycopenal.

Lycopene and apo-12'-lycopenal reduce cell proliferation and alter cell cycle progression in human prostate cancer cells.[Pubmed:21207319]

Nutr Cancer. 2011;63(2):256-63.

Lycopene is associated with a reduced risk of prostate cancer. However, lycopene may not be wholly responsible for the effects seen in vivo or in cell culture systems. Apo-lycopenals or other lycopene metabolites, whether produced by cleavage enzymes within the body or consumed with tomato products, can be found in tissues at concentrations equivalent to physiological retinoid concentrations. Therefore, it is plausible that lycopenoids, like retinoids, are bioactive within tissues. Androgen-independent DU145 prostate cancer cells were treated with lycopene, apo-8'-lycopenal, or apo-12'-lycopenal. DU145 cell proliferation was significantly reduced by supra-physiological levels of lycopene and apo-12'-lycopenal, in part, through alteration of the normal cell cycle. Levels of the gap junction protein, connexin 43, were unaltered by lycopene or apo-lycopenal treatment while cell apoptosis rates significantly decreased. We further confirmed that connexin 43 protein levels were unaltered by lycopene treatment in mouse embryonic fibroblasts, or in Dunning R3327-H rat prostate tumor. The present data indicate that lycopene and apo-12'-lycopenal reduce the proliferation of prostate cancer cells, in part, by inhibiting normal cell cycle progression.

Lycopene epoxides and apo-lycopenals formed by chemical reactions and autoxidation in model systems and processed foods.[Pubmed:20492100]

J Food Sci. 2009 Nov-Dec;74(9):C674-82.

To gain a better understanding of the reactions and the underlying mechanisms of the oxidative degradation of lycopene, the products formed by epoxidation with m-chloroperbenzoic acid (MCPBA), oxidative cleavage with KMnO(4), and autoxidation in low-moisture and aqueous model systems, under light exposure, at ambient temperature were identified. The presence of oxidation products was also verified in processed products (tomato juice, tomato paste, tomato puree, guava juice, "goiabada"). A total of 8 lycopene epoxides and a cyclolycopene diol were formed by the reaction of lycopene with MCPBA and 6 apo-lycopenals were produced with KMnO(4). Some of these oxidation products were not detected in the model systems and in the foods analyzed, but the acid-catalyzed rearrangement product 2,6-cyclolycopene-1,5-diol and apo-12'-lycopenal were found in all model and food systems and lycopene-1,2-epoxide and 2,6-cyclolycopene-1,5-epoxide were found in the model systems and in all but 1 ("goiabada") of the 5 foods analyzed. Other epoxides and apo-lycopenals were found in some systems. The inability to detect an intermediate product could be due to a fast turn over. Increased Z-isomerization was also observed and Z-isomers of the oxidation products were detected.

Apo-8'-lycopenal and apo-12'-lycopenal are metabolic products of lycopene in rat liver.[Pubmed:16702320]

J Nutr. 2006 Jun;136(6):1552-7.

The health benefits of lycopene as an anticarcinogenic compound have been widely studied but little is known about the metabolic products of lycopene produced in vivo. We investigated lycopene metabolites in the liver of F344 male rats that had been prefed a lycopene-containing diet (0.25 g lycopene/kg diet). After 30 d of feeding, they were given a single oral dose of 14C-labeled lycopene (421.8 kBq). The metabolic products of both nonradioactive and 14C-labeled lycopene in rat liver were extracted and separated using HPLC and analyzed by UV/VIS spectrometry, online radioactive detection, and off-line and in-line positive ion electrospray ionization MS. Among a number of metabolite products formed, we identified apo-8'-lycopenal (lambdamax = 473 nm and m/z = 417). The putative compound, apo-12'-lycopenal, was detected but no apo-10'-lycopenal was present. A number of other very polar, short-chain and/or short chromophore compounds with UV/VIS absorption <300 nm were present but were not characterized. These data show that lycopene is cleaved in vivo by rats at different positions to produce apo-12'-lycopenal, and other unidentified metabolites in addition to apo-8'-lycopenal. Apo-8'-lycopenal and the putative apo-12'-lycopenal are identified as lycopene metabolites in rat liver in vivo.

Formation of cleavage products by autoxidation of lycopene.[Pubmed:11269700]

Lipids. 2001 Feb;36(2):191-9.

The cleavage products formed by autoxidation of lycopene were evaluated in order to elucidate possible oxidation products of lycopene in biological tissues. Lycopene solubilized at 50 microM in toluene, aqueous Tween 40, or liposomal suspension was oxidized by incubating at 37 degrees C for 72 h. Among a number of oxidation products formed, eight products in the carbonyl compound fraction were identified as 3,7,11 -trimethyl-2,4,6,10-dodecatetraen-1-al, 6,10,14-trimethyl-3,5,7,9,13-pentadecapentaen-2-one, acycloretinal, apo-14'-lycopenal, apo-12'-lycopenal, apo-10'-lycopenal, apo-8'-lycopenal, and apo-6'-lycopenal. These correspond to a series of products formed by cleavage in the respective 11 conjugated double bonds of lycopene. The maximal formation of acycloretinal was 135 nM in toluene, 49 nM in aqueous Tween 40, and 64 nM in liposomal suspension. Acycloretinoic acid was also formed by autoxidation of lycopene, although its formation was lower in the aqueous media than in toluene. The pig liver homogenate had the ability to convert acycloretinal to acycloretinoic acid, comparable to the conversion of all-transretinal to all-trans-retinoic acid. These results suggest that lycopene might be cleaved to a series of apolycopenals and short-chain carbonyl compounds under the oxidative conditions in biological tissues and that acycloretinal is further enzymatically converted to acycloretinoic acid.

Keywords:

Apo-12'-Lycopenal,1071-52-9,Natural Products, buy Apo-12'-Lycopenal , Apo-12'-Lycopenal supplier , purchase Apo-12'-Lycopenal , Apo-12'-Lycopenal cost , Apo-12'-Lycopenal manufacturer , order Apo-12'-Lycopenal , high purity Apo-12'-Lycopenal

Online Inquiry for:

      Fill out the information below

      • Size:Qty: - +

      * Required Fields

                                      Result: