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MedKoo Cat#: 463289 | Name: Apocarotenal
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Apocarotenal, or trans-β-apo-8'-carotenal, is a carotenoid found in spinach and citrus fruits. Like other carotenoids, apocarotenal plays a role as a precursor of vitamin A, even though it has 50% less pro-vitamin A activity than β-carotene. The empirical chemical formula for apocarotenal is C30H40O. Apocarotenal has an orange to orange-red colour and is used in foods, pharmaceuticals and cosmetic products. Depending on the product forms, apocarotenal is used in fat based food (margarine, sauces, salad dressing), beverages, dairy products and sweets. Its E number is E160e and it is approved for usage as a food additive in the US, EU. Australia and New Zealand.

Chemical Structure

Apocarotenal
Apocarotenal
CAS#1107-26-2

Theoretical Analysis

MedKoo Cat#: 463289

Name: Apocarotenal

CAS#: 1107-26-2

Chemical Formula: C30H40O

Exact Mass: 416.3079

Molecular Weight: 416.65

Elemental Analysis: C, 86.48; H, 9.68; O, 3.84

Price and Availability

Size Price Availability Quantity
50mg USD 350.00 2 Weeks
100mg USD 550.00 2 Weeks
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Related CAS #
No Data
Synonym
Apocarotenal; CI 40820; CI-40820; CI40820; C Orange 16; Food orange 6; C.I. Food Orange 6; trans-β-apo-8'-carotenal;
IUPAC/Chemical Name
(2E,4E,6E,8E,10E,12E,14E,16E)-2,6,11,15-tetramethyl-17-(2,6,6-trimethylcyclohex-1-en-1-yl)heptadeca-2,4,6,8,10,12,14,16-octaenal
InChi Key
DFMMVLFMMAQXHZ-DOKBYWHISA-N
InChi Code
InChI=1S/C30H40O/c1-24(13-8-9-14-25(2)16-11-18-27(4)23-31)15-10-17-26(3)20-21-29-28(5)19-12-22-30(29,6)7/h8-11,13-18,20-21,23H,12,19,22H2,1-7H3/b9-8+,15-10+,16-11+,21-20+,24-13+,25-14+,26-17+,27-18+
SMILES Code
C/C(C=O)=C\C=C\C(C)=C\C=C\C=C(\C=C\C=C(\C=C\C1=C(CCCC1(C)C)C)C)C
Appearance
Solid powder
Purity
>95% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 416.65 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
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PMID: 31180245. 5: Durojaye BO, Riedl KM, Curley RW Jr, Harrison EH. Uptake and metabolism of β-apo-8'-carotenal, β-apo-10'-carotenal, and β-apo-13-carotenone in Caco-2 cells. J Lipid Res. 2019 Jun;60(6):1121-1135. doi: 10.1194/jlr.M093161. Epub 2019 Mar 6. PMID: 30846527; PMCID: PMC6547639. 6: Alcalde E, Cerdá-Olmedo E, Al-Babili S. Apocarotenoids produced from β-carotene by dioxygenases from Mucor circinelloides. Microbiology (Reading). 2019 Apr;165(4):433-438. doi: 10.1099/mic.0.000762. Epub 2019 Feb 14. PMID: 30762519. 7: Serra S, De Simeis D. Fungi-Mediated Biotransformation of the Isomeric Forms of the Apocarotenoids Ionone, Damascone and Theaspirane. Molecules. 2018 Dec 21;24(1):19. doi: 10.3390/molecules24010019. PMID: 30577583; PMCID: PMC6337586. 8: Vega-Teijido M, Cantero J, Rodrigo MJ, López C, Zunini MP. An in silico study of the citrus dioxygenases CCD4 family substrates. J Biomol Struct Dyn. 2019 May;37(8):2086-2097. doi: 10.1080/07391102.2018.1477619. Epub 2018 Nov 5. PMID: 30044177. 9: Demurtas OC, Frusciante S, Ferrante P, Diretto G, Azad NH, Pietrella M, Aprea G, Taddei AR, Romano E, Mi J, Al-Babili S, Frigerio L, Giuliano G. Candidate Enzymes for Saffron Crocin Biosynthesis Are Localized in Multiple Cellular Compartments. Plant Physiol. 2018 Jul;177(3):990-1006. doi: 10.1104/pp.17.01815. Epub 2018 May 29. PMID: 29844227; PMCID: PMC6053014. 10: Ehlers F, Scholz M, Oum K, Lenzer T. Excited-state dynamics of 3,3'-dihydroxyisorenieratene and (3R,3'R)-zeaxanthin: Observation of vibrationally hot S0 species. Arch Biochem Biophys. 2018 May 15;646:137-144. doi: 10.1016/j.abb.2018.03.035. Epub 2018 Mar 30. PMID: 29605493. 11: Schaub P, Rodriguez-Franco M, Cazzonelli CI, Álvarez D, Wüst F, Welsch R. Establishment of an Arabidopsis callus system to study the interrelations of biosynthesis, degradation and accumulation of carotenoids. PLoS One. 2018 Feb 2;13(2):e0192158. doi: 10.1371/journal.pone.0192158. PMID: 29394270; PMCID: PMC5796706. 12: Hostetler GL. Determination of Lutein and β-Carotene in Infant Formula and Adult Nutritionals by Ultra-High-Performance Liquid Chromatography: Single- Laboratory Validation, First Action 2016.13. J AOAC Int. 2017 May 1;100(3):768-781. doi: 10.5740/jaoacint.16-0386. PMID: 28468699. 13: Bohn T. Bioactivity of Carotenoids - Chasms of Knowledge. Int J Vitam Nutr Res. 2017 Mar;87(1-2):5-9. doi: 10.1024/0300-9831/a000400. Epub 2017 Feb 10. PMID: 28186459. 14: Ahrazem O, Gómez-Gómez L, Rodrigo MJ, Avalos J, Limón MC. Carotenoid Cleavage Oxygenases from Microbes and Photosynthetic Organisms: Features and Functions. Int J Mol Sci. 2016 Oct 26;17(11):1781. doi: 10.3390/ijms17111781. PMID: 27792173; PMCID: PMC5133782. 15: Jain M, Srivastava PL, Verma M, Ghangal R, Garg R. De novo transcriptome assembly and comprehensive expression profiling in Crocus sativus to gain insights into apocarotenoid biosynthesis. Sci Rep. 2016 Mar 3;6:22456. doi: 10.1038/srep22456. PMID: 26936416; PMCID: PMC4776159. 16: Mordi RC, Walton JC. Identification of products from canthaxanthin oxidation. Food Chem. 2016 Apr 15;197(Pt A):836-40. doi: 10.1016/j.foodchem.2015.11.053. Epub 2015 Nov 12. PMID: 26617024. 17: Lätari K, Wüst F, Hübner M, Schaub P, Beisel KG, Matsubara S, Beyer P, Welsch R. Tissue-Specific Apocarotenoid Glycosylation Contributes to Carotenoid Homeostasis in Arabidopsis Leaves. Plant Physiol. 2015 Aug;168(4):1550-62. doi: 10.1104/pp.15.00243. Epub 2015 Jul 1. PMID: 26134165; PMCID: PMC4528739. 18: Ehlers F, Scholz M, Schimpfhauser J, Bienert J, Oum K, Lenzer T. Collisional relaxation of apocarotenals: identifying the S* state with vibrationally excited molecules in the ground electronic state S(0)*. Phys Chem Chem Phys. 2015 Apr 28;17(16):10478-88. doi: 10.1039/c4cp05600k. PMID: 25802898. 19: Yamano Y, Ematsu K, Kurimoto H, Maoka T, Wada A. Total synthesis of gobiusxanthin stereoisomers and their application to determination of absolute configurations of natural products: revision of reported absolute configuration of epigobiusxanthin. Mar Drugs. 2014 Dec 30;13(1):159-72. doi: 10.3390/md13010159. PMID: 25561412; PMCID: PMC4306930. 20: Sui X, Kiser PD, Che T, Carey PR, Golczak M, Shi W, von Lintig J, Palczewski K. Analysis of carotenoid isomerase activity in a prototypical carotenoid cleavage enzyme, apocarotenoid oxygenase (ACO). J Biol Chem. 2014 May 2;289(18):12286-99. doi: 10.1074/jbc.M114.552836. Epub 2014 Mar 19. PMID: 24648526; PMCID: PMC4007427.