References of 2,4,6,8,10,12,14,16,18-Eicosanonaenedioicacid, 4,8,13,17-tetramethyl-, 1-methyl ester,(2E,4Z,6E,8E,10E,12E,14E,16E,18E)-
Title: Bixins
Literature References: Carotenoid carboxylic acids isolated from seeds of
Bixa orellana L.,
Bixaceae; principal pigments of the crude coloring extract, annatto,
q.v. The natural product is the
cis-form. Isomerization to the more stable all-
trans-form occurs upon heating or commercial extraction. Isoln: J. B. Boussingault,
Ann. Chim. Phys. 28, 440 (1825). Isomerization studies: J. Herzig, F. Faltis,
Ann. 431, 40 (1923); P. Karrer
et al., Helv. Chim. Acta 12, 741 (1929). Structural studies: R. Kuhn
et al., ibid. 11, 427 (1928);
12, 64, 904 (1929);
Ber. 64, 1732 (1931);
65, 646, 1873 (1932). NMR determn of stereochemistry: M. S. Barber
et al., J. Chem. Soc. 1961, 1625. Properties of bixin and norbixin: J. F. Reith, J. W. Gielen,
J. Food Sci. 36, 861 (1971). 1H and 13C NMR, MS, and x-ray crystal structure determn: D. R. Kelly
et al., J. Chem. Res. Miniprint 10, 2640 (1996). HPLC analysis of food coloring formulations: M. J. Scotter
et al., J. Agric. Food Chem. 46, 1031 (1998). Biosynthesis and prodn in genetically engineered
E. coli (stereo unspecified): F. Bouvier
et al., Science 300, 2089 (2003). Review of
cis-trans isomerization and stereochemistry: L. Zechmeister,
Chem. Rev. 34, 267-344 (1944); of chemistry and extraction from annatto: H. D. Preston, M. D. Rickard,
Food Chem. 5, 47-56 (1980).
Derivative Type: cis-Form
CAS Registry Number: 6983-79-5
CAS Name: (2
E,4
Z,6
E,8
E,10
E,12
E,14
E,16
E,18
E)-4,8,13,17-Tetramethyl-2,4,6,8,10,12,14,16,18-eicosanonaenedioic acid monomethyl ester
Synonyms: 9-
cis-6,6￠-diapo-y,y-carotenedioic acid monomethyl ester; 6￠-methyl hydrogen (9￠
Z)-6,6￠-diapocarotene-6,6￠-dioate; a-bixin; labile bixin
Molecular Formula: C25H30O4
Molecular Weight: 394.50
Percent Composition: C 76.11%, H 7.66%, O 16.22%
Properties: Dark purple, lustrous crystals from ethanol + chloroform or dichloromethane + acetone, mp 190 ± 1°; dec 200.3 ± 0.6°. Absorption max (chloroform): 502, 471 nm (log e = 5.02, 5.07).
Melting point: mp 190 ± 1°
Absorption maximum: Absorption max (chloroform): 502, 471 nm (log e = 5.02, 5.07)
Derivative Type: trans-Form
CAS Registry Number: 39937-23-0
CAS Name: (2
E,4
E,6
E,8
E,10
E,12
E,14
E,16
E,18
E)-4,8,13,17-Tetramethyl-2,4,6,8,10,12,14,16,18-eicosanonaenedioic acid monomethyl ester
Synonyms: all
-trans bixin; b-bixin; isobixin; stable bixin
Molecular Formula: C25H30O4
Molecular Weight: 394.50
Percent Composition: C 76.11%, H 7.66%, O 16.22%
Properties: Orange to purple plates from acetone, mp 204-206° (dec). Absorption max (chloroform): 507, 476 nm (E1%1cm 2970 ±40, 3240 ±50). Sol in oil.
Melting point: mp 204-206°
Absorption maximum: Absorption max (chloroform): 507, 476 nm
Derivative Type: a-Norbixin
CAS Registry Number: 626-76-6
CAS Name: (2
E,4
E,6
E,8
E,10
E,12
E,14
E,16
Z,18
E)-4,8,13,17-Tetramethyl-2,4,6,8,10,12,14,16,18-eicosanonaenedioic acid
Synonyms: 9-
cis-6,6￠-diapo-y,y-carotenedioic acid
Molecular Formula: C24H28O4
Molecular Weight: 380.48
Percent Composition: C 75.76%, H 7.42%, O 16.82%
Properties: No melting observed ￡280°; yellow coloring observed at 240°; black coloring (carbonization) at 3280°. Absorption max (chloroform): 499, 468 nm (E1%1cm 2200 ±30, 2470 ±30).
Absorption maximum: Absorption max (chloroform): 499, 468 nm (E1%1cm 2200 ±30, 2470 ±30)
Derivative Type: b-Norbixin
CAS Registry Number: 542-40-5
CAS Name: (All-
E)-4,8,13,17-tetramethyl-2,4,6,8,10,12,14,16,18-eicosanonaenedioic acid
Synonyms: 6,6￠-diapo-y,y-carotenedioic acid; all-trans norbixin
Molecular Formula: C24H28O4
Molecular Weight: 380.48
Percent Composition: C 75.76%, H 7.42%, O 16.82%
Properties: No melting observed ￡300°; red color darkens 3250°. Absorption max (chloroform): 506, 475 nm; (0.1 N NaOH): 486, 457 nm. Sol in H2O.
Absorption maximum: Absorption max (chloroform): 506, 475 nm; (0.1 N NaOH): 486, 457 nm
Use: Food coloring; imparts a golden yellow color to butter and cheese.
