Basic information
- CAS
432-68-8- Standard SMILES
CC1=C(/C=C/C(C)=C/C=C/C(C)=C/C=C/C=C(C)/C=C/C=C(C)/C=C/C2=C(C)C(=O)CCC2(C)C)C(C)(C)CCC1- InChIKey
QXNWZXMBUKUYMD-QQGJMDNJSA-N- Molecular formula
- C40H54O
- Average molar mass
- 550.9 g/mol
- Monoisotopic mass
- 550.41746635
Overview
Echinenone is a carotenone that is beta-carotene in which the 4 position has undergone formal oxidation to afford the corresponding ketone. Isolated as orange-red crystals, it is widely distributed in marine invertebrates. It has a role as a cofactor, an animal metabolite, a marine metabolite and a bacterial metabolite. It derives from a hydride of a beta-carotene.
Names & identifiers
- Preferred name
- Echinenone
- IUPAC
- 2,4,4-trimethyl-3-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-3,7,12,16-tetramethyl-18-(2,6,6-trimethylcyclohexen-1-yl)octadeca-1,3,5,7,9,11,13,15,17-nonaenyl]cyclohex-2-en-1-one
- English name
- Echinenone
- Molecular formula
- C40H54O
- Molecular weight
- 550.86
Names & synonyms
Echinenone432-68-8all-trans-Echinenoneaphaninmyoxanthin4-oxo-beta-carotene4-keto-beta-caroteneLJ5IO02MNQ2,4,4-trimethyl-3-[(1E,3E,5E,7E,9E,11E,13E,15E,17E)-3,7,12,16-tetramethyl-18-(2,6,6-trimethylcyclohexen-1-yl)octadeca-1,3,5,7,9,11,13,15,17-nonaenyl]cyclohex-2-en-1-oneCHEBI:4746DTXSID101026555beta-Echinenone
Show more names
Einecs 207-083-4β,β-Caroten-4-one?,?-caroten-4-oneEchinenone (In Solution)9-cis-β,β-Carotene-4-one9'-cis-β,β-Carotene-4-one
2,4,4-trimethyl-3-((1E,3E,5E,7E,9E,11E,13E,15E,17E)-3,7,12,16-tetramethyl-18-(2,6,6-trimethylcyclohexen-1-yl)octadeca-1,3,5,7,9,11,13,15,17-nonaenyl)cyclohex-2-en-1-oneRefChem:920807DTXCID90911095207-083-4beta,beta-Caroten-4-oneEchinenone (Technical Grade).beta.,.beta.-Caroten-4-oneUNII-LJ5IO02MNQ
Database identifiers
- CAS
Properties
Computed structural properties
- XLogP
- 12.5
- Topological polar surface area
- 17.1 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 1
- Rotatable bonds
- 10
- Heavy atoms
- 41
- Formal charge
- 0
- Complexity
- 1,300
Experimental & physicochemical properties
LipidsLipids -> Prenol Lipids [PR] -> Isoprenoids [PR01] -> C40 isoprenoids (tetraterpenes) [PR0107]
Physicochemical properties
- Melting point
- 178 · 178-180°
- Boiling point
- 685.3 · 685.3±25.0 °C(Predicted)
- Density
- 0.972 · 0.972±0.06 g/cm3(Predicted)
- storage temp.
- -20 °C · -20°C
- solubility
- Chloroform (Slightly), Diethyl Ether (Slightly), Methanol (Slightly)
- form
- Solid
- color
- Dark Red to Very Dark Red
- λmax
- 459 nm±5 · λ: 459 nm±5 nm Amax
- BRN
- 2030114 · 2030114
- Stability
- Light Sensitive, Temperature Sensitive
- InChIKey
- QXNWZXMBUKUYMD-QQGJMDNJSA-N
- SMILES
- CC(/C=C/C1=C(C)C(CCC1(C)C)=O)=C\C=C\C(C)=C\C=C\C=C(C)\C=C\C=C(\C=C\C2=C(C)CCCC2(C)C)C
Safety & regulation
Safety data
- wgk
- 3
- Storage Class
- 11 - Combustible Solids
Chemistry & industry
Applications
UsesEchinenone may be used as an external standard for the extraction of carotenoid from plasma samples. It may also been used as an internal standard, added to samples for extraction and quantification.
General DescriptionEchinenone is a carotenoid with a conjugated carbonyl group. Echinenone (4-keto-β-carotene) is a monoketo compound, is an intermediate between β-carotene and canthaxanthin in animals. It is one of the major carotenoids of Anabaena sp., and also present in Micrococcus roseus. It is located in the thylakoid membrane of Anabaena. The conversion of β-carotene to echinenone is catalysed by CrtO, a β-carotene ketolase.
Suppliers15 total
南京世洲生物科技有限公司025-85560043 15850508050 · [email protected]
上海惠诚生物科技有限公司60498804 18930850192 · [email protected]
成都超九八生物科技有限公司13348960310 13348960310 · [email protected]
江苏星科元信息科技有限公司400-605-7200 15335295587
上海纽雀客生物科技有限公司13916276291 · [email protected]
上海赛可锐生物科技有限公司021-58000709 13120558703 · [email protected]
河北茹麒科技有限公司176-03256889 17603256889 · [email protected]
TargetMol 中国（陶术生物）400-821-0310 15002144251 · [email protected]
Sigma-Aldrich西格玛奥德里奇(上海)贸易有限公司021-61415566 800-8193336 · [email protected]
Related reactions
1 records
Compound notes
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