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73341

Sigma-Aldrich

Echinenone

≥95.0% (HPLC), solid

Synonym(s):

β,β-Caroten-4-one

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About This Item

Empirical Formula (Hill Notation):
C40H54O
CAS Number:
432-68-8
Molecular Weight:
550.86
Beilstein:
2030114
EC Number:
207-083-4
MDL number:
MFCD06656303
UNSPSC Code:
12352202
PubChem Substance ID:
329764812
NACRES:
NA.32

product name

Echinenone, ≥95.0% (HPLC)

Assay

≥95.0% (HPLC)

form

solid

λ

in hexane (with 2% dichloromethane)

UV absorption

λ: 459 nm±5 nm Amax

storage temp.

−20°C

SMILES string

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

InChI

1S/C40H54O/c1-30(18-13-20-32(3)23-25-36-34(5)22-15-28-39(36,7)8)16-11-12-17-31(2)19-14-21-33(4)24-26-37-35(6)38(41)27-29-40(37,9)10/h11-14,16-21,23-26H,15,22,27-29H2,1-10H3/b12-11+,18-13+,19-14+,25-23+,26-24+,30-16+,31-17+,32-20+,33-21+

InChI key

QXNWZXMBUKUYMD-QQGJMDNJSA-N

General description

Echinenone 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.

Application

Echinenone 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.

Biochem/physiol Actions

Echinenone binds to glocobacter rhodopsin and functions as a light harvesting antenna in Gloeobacter violaceous.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Que Chen et al.
Photochemistry and photobiology, 93(3), 772-781 (2017-05-14)
Proteorhodopsins are light-driven proton pumps that occur widespread in Nature, where they function predominantly in environments with high incident irradiance. Their maximal absorbance is usually in the blue range, but can be extended into the (far)red range of the electromagnetic
Effects of exercise and training in hypoxia on antioxidant/pro-oxidant balance
Pialoux V, et al.
European Journal of Clinical Nutrition, 60(12), 1345-1345 (2006)
Paula Mapelli-Brahm et al.
Food chemistry, 300, 125232-125232 (2019-07-29)
The mechanisms of main tomato carotenes (phytoene, phytofluene, lycopene and β-carotene) intestinal absorption are still only partly understood. We thus compared carotene bioavailability in mice after gavage with carotene-rich oil-in-water emulsions. We also determined each carotene absorption profile along the
Fernando Muzzopappa et al.
Nature plants, 5(10), 1076-1086 (2019-09-19)
The photoactive orange carotenoid protein (OCP) is a blue-light intensity sensor involved in cyanobacterial photoprotection. Three OCP families co-exist (OCPX, OCP1 and OCP2), having originated from the fusion of ancestral domain genes. Here, we report the characterization of an OCPX
The cyanobacterium Anabaena sp. PCC 7120 has two distinct beta-carotene ketolases: CrtO for echinenone and CrtW for ketomyxol synthesis
Mochimaru M, et al.
Febs Letters, 579(27), 6111-6114 (2005)
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