α-Zeacarotene

α-Zeacarotene
Names
	IUPAC name (6R)-7',8'-Dihydro-ε,psi-carotene
	Systematic IUPAC name (6R)-6-[(1E,3E,5E,7E,9E,11E,13E,15E,19E)-3,7,12,16,20,24-hexamethylpentacosa-1,3,5,7,9,11,13,15,19,23-decaenyl]-1,5,5-trimethylcyclohexene
Identifiers
CAS Number	50657-19-7 ;
3D model (JSmol)	Interactive image;
Beilstein Reference	2512967
ChEBI	CHEBI:35063 ;
ChemSpider	4445511 ;
KEGG	C14146;
PubChem CID	6441660;
CompTox Dashboard (EPA)	DTXSID201317733 ;
	InChI InChI=1S/C40H58/c1-32(2)18-13-21-35(5)24-15-26-36(6)25-14-22-33(3)19-11-12-20-34(4)23-16-27-37(7)29-30-39-38(8)28-17-31-40(39,9)10/h11-12,14,16,18-20,22-25,27-30,39H,13,15,17,21,26,31H2,1-10H3/b12-11+,22-14+,23-16+,30-29+,33-19+,34-20+,35-24+,36-25+,37-27+/t39-/m0/s1 Key: IGABZIVJSNQMPZ-DWQNOKSTSA-N [CAS]; InChI=1S/C40H58/c1-32(2)18-13-21-35(5)24-15-26-36(6)25-14-22-33(3)19-11-12-20-34(4)23-16-27-37(7)29-30-39-38(8)28-17-31-40(39,9)10/h11-12,14,16,18-20,22-25,27-30,39H,13,15,17,21,26,31H2,1-10H3/b12-11+,22-14+,23-16+,30-29+,33-19+,34-20+,35-24+,36-25+,37-27+/t39-/m0/s1 Key: ANVAOWXLWRTKGA-JLTXGRSLBQ;
	SMILES CC1=CCCC([C@H]1/C=C/C(=C/C=C/C(=C/C=C/C=C(\C)/C=C/C=C(\C)/CC/C=C(\C)/CCC=C(C)C)/C)/C)(C)C;
Properties
Chemical formula	C40H58
Molar mass	538.45385
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). verify (what is ?) Infobox references

α-Zeacarotene (alpha-zeacarotene) is a form of carotene with a β-ionone ring at one end and a ζ-ionone ring at the opposite end. It is an intermediate in the biosynthesis of various carotenoids and plays a crucial role in the metabolic pathway leading to the production of lycopene and other important carotenoids.^[1]

Chemical structure and properties

The molecular formula of α-zeacarotene is C40H58, with an average molecular weight of 538.89 g/mol. Its IUPAC name is 6-[(1E,3Z,5E,7E,9E,11Z,13E,15E,19Z)-3,7,12,16,20,24-hexamethylpentacosa-1,3,5,7,9,11,13,15,19,23-decaen-1-yl]-1,5,5-trimethylcyclohex-1-ene. The compound is an isomer of β-zeacarotene and exists in both (6R)-isomer and (trans)-isomer forms.

α-Zeacarotene is characterized by a predicted boiling point of 637.98 °C at 760 mm Hg and an estimated water solubility of 8.7e-14 mg/L at 25°C, indicating very low solubility in water. Its predicted logP values range from 9.66 to 15.27, highlighting its lipophilic nature.^[2]

Biological role and function

In biological systems, α-zeacarotene functions as an intermediate in the biosynthesis of other carotenoids, including lycopene and β-carotene. It is primarily located in the cytoplasm and cell membranes. The compound also plays a role in cell signaling and lipid metabolism, particularly within the lipid peroxidation and fatty acid metabolism pathways.

α-Zeacarotene has been detected in various plant sources, particularly cereals such as corn and breakfast cereals, and is considered both an endogenous (naturally occurring within organisms) and exogenous (obtained through diet) nutrient.^[3]

Industrial applications

In addition to its biological roles, α-zeacarotene has applications in the manufacturing industry, particularly as a fluid processing agent and surfactant. It also functions as an emulsifier, playing a role in stabilizing mixtures in industrial processes.^[4]

Synonyms and identification

Synonyms: α-Zeacarotene is also known by several other names, including 7',8'-dihydro-epsilon,Psi-carotene, 7',8'-dihydro-e,Y-carotene, and Zeacarotene.

References

^ "Human Metabolome Database: Showing metabocard for alpha-Zeacarotene (HMDB0036909)". hmdb.ca. Retrieved October 15, 2024.
^ PubChem. "7',8'-Dihydro-e,y-carotene". pubchem.ncbi.nlm.nih.gov. Retrieved October 15, 2024.
^ "α-Zeacarotene in Foods". FooDB.
^ "(5′cis,9cis,13′cis)-4,5-Didehydro-5,6,7′,8′-tetrahydro-β,ψ-carotene | C40H58". www.chemspider.com. Retrieved October 15, 2024.

[1] "Human Metabolome Database: Showing metabocard for alpha-Zeacarotene (HMDB0036909)". hmdb.ca. Retrieved October 15, 2024.

[2] PubChem. "7',8'-Dihydro-e,y-carotene". pubchem.ncbi.nlm.nih.gov. Retrieved October 15, 2024.

[3] "α-Zeacarotene in Foods". FooDB.

[4] "(5′cis,9cis,13′cis)-4,5-Didehydro-5,6,7′,8′-tetrahydro-β,ψ-carotene | C40H58". www.chemspider.com. Retrieved October 15, 2024.

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