Carotenoids nomenclature

The mixture was next quenched with water and the resulting precipitated oil taken up in pentane, dried with sodium sulfate, and distilled under vacuum. The product was collected at 100° to 110°C at 0.001 mm/Hg, nD24-5 1.50 60. The infrared and ultraviolet spectrum corresponded to 10,ll-didehydro-9-ethoxy-9,12-dihydroretinol acetate, using carotenoid nomenclature based on the parent compound retinol. 

Some amendments to the IUPAC-IUB rules for carotenoid nomenclature have been made, in particular to include the 7-ring end-group (1) and some C37 (trinor) carotenoids.1 Rules have also been presented for the nomenclature of quinones with isoprenoid side-chains.2... 

New rules for carotenoid nomenclature are now approved (98). In the semirational names a double Greek prefix is used to indicate the C9 end groups. Scheme 1. Thus in the new nomenclatme a-carotene is P,s-carotene. The numbering of the carbon skeleton is indicated and further principles of the new nomenclature rules are illustrated by the semirational name of neoxanthin (1) = (35,5R,6i ,3 5,5 i ,6 S)-5, 6 -epoxy-6,7-didehydro-5,6,5, 6 -tetradehydro-P,P-carotene-3,5,3 -triol. 

WEEDON B c L and MOSS G (1995) Structure, stereochemistry and nomenclature , in Britton G, Pfander H and Liaaen-Jensen S, Carotenoids, vol. la, Basel, Birkhauser 27—44. 

Some 117 naturally occurring apo-carotenoids, 88 of which have been fully identified and another 6 naturally occurring seco-carotenoids have been referenced as carotenoids, thus representing around 15% of the carotenoids numbered to date (see Figure 3.3.1). This subfamily of carotenoids would be even larger if we consider the retinoids andnorisoprenoids. However, these compounds are excluded by nomenclature rules that dictate that they are not deemed to be carotenoids because of the absence of two central methyl groups (at C20 and C20 ). Retinoic acid, retinal. 

IUPAC Commission on the Nomenclature of Organic Chemistry and IUPAC-IUB Commission on Biochemical Nomenclature (1971). Carotenoids. O. Isler. Basel, Switzerland Birkhauser Verlag, pp. 851-864. 

Weedon, B. C. L. and G. P. Moss (1995). Structure and nomenclature. Carotenoids, Isolation and Analysis. G. Britton, S. Liaaen-Jensen and H. Pfander, eds. Basel, Switzerland Birkauser Verlag, pp. 1A. 

Tentative rules for the nomenclature of carotenoids /. Biol Chem. (1972) 247, 2633-2643 Revision, Biochemistry (1975) 14, 1803 Pure Appl Chem. (1975) 41, 407-431... 

Nomenclature of Carbohydrates http //www.chcm.qinul.ac.Lik/iupac/2carb/ Nomenclature of Carotenoids http //www.chcin.qmul.ac.uk/iiipac/carot/ Nomenclature and Symbols for Folic Acid and Related Compounds http //www. chem.qmul.ac.uk/iupac/misc/folic.html... 

Table 1 Chemical Nomenclature and Provitamin A Activity of Some Common Carotenoids of Plant Foods...

IUPAC-IUB. IUPAC commission on the nomenclature of organic chemistry and IUPAC-IUB commission on biochemical nomenclature tentative rules for the nomenclature of carotenoids. Biochemistry 10 4827-4837, 1971. 

Moss GP. lUPAC-IUB loint commission biochemical nomenclature (ICBN). Nomenclature of Carotenoids, http //www.chem.qmul. ac. uk/iupac/carot/. 

A new type of end-group was detected in a carotenoid from the fungus Calo-scypha fulgens Using the provional lUPAC systematic nomenclature this compound is called /i,y-carotene, (19). Its structure was proved" by synthesis from y-ionone using standard methods. y,y-Carotene was also synthesized, though as yet it has not been found in nature. 

The carotenoids are a class of hydrocarbons (carotenes) and their oxygenated derivatives (xanthophylls) that consist of eight isoprenoid units joined in such a manner that the arrangement of the units is reversed at the center of the molecule, so that the two central methyl groups are in a 1,6-positional relationship and the remaining nonterminal methyl groups are in a 1,5-positional relationship. Their nomenclature has been standardized by lUPAC [http //www.chem.qmul.ac.uk/iupac/carot/], and their formal names are all based on the term carotene. ... 

Other Commissions on Nomenclature of the lUPAC have not been inactive. In biochemistry reports have been made on steroids (II), amino acids (12), vitamins (8), and carotenoids (7). A report on the nomenclature of macro-molecular compounds has been approved (6). 

International Union of Pure and Applied Chemistry, /. Am. Chem. Soc. 82, 5575-84 (I960) Definitive rules for the nomenclature of amino acids, steroids, vitamins, and carotenoids (lUPAC). 

The Nomenclature of the Carotenoid Pigments. Report of the Committee on Biochemical Nomenclature of the National Research Council, accepted by the Committee on Nomenclature, Spelling, and Pronunciation of the American Chemical Society. No charge. 

Carotenoids. A preliminary report on nomenclature of the carotenoids, drawn by the Committee on Biochemical Nomenclature of the National Research Council of the United States, was published in 1946 (11). P. Karrer, president of the commission at that time, with this report as a basis, presented a project to the commission (9) containing a few modifications and extensions of the American draft. KarrePs (5) text was discussed at the London conference in 1947 at a meeting held by the joint commissions for nomenclature of organic chemistry and biological chemistry. A few slight modifications were made, and this new text was adopted by the Council of the Union in 1947. It has been published by several periodicals (5) since that time. 

Eine im Jahre 1946 veroffentlichte Nomenklatur fiir Carotinoide [B. L. Wehm-hoff , Nomenclature of Carotenoid Pigments", Chem. and Engin. News 24, 1235 (1946)] bezieht sich nur auf die natiirlichen Eigmente der Begriff, Carotinoide" wurde nicht klar umgrenzt. 

Isler 0(1971) Carotenoids. Birkhauser Verlag, Basel and Stuttgart lUPAC and lUB (1971) lUPAC commission on the nomenclature of organic chemistry and lUPAC-IUB commission on biochemical nomenclature Tentative rules for the nomenclature of carotenoids. Biochemistry 10 4827-4837 lUPAC and lUB (1975) Nomenclature of carotenoids (Recommendations 1974). Biochemistry 14 1803-1804 Jablonski A Z (1935) Uber den Mechanismus des Photo-lumineszenz von Farbstoffphosphoren. Zs Phys 94 38 6 Jackson JB and Crofts AR (1969) The high energy state in chromatophores from Rhodopseudomonas sphaeroides. FEBS Lett 4 185-189... 

Palmer LS (1934) The biological and chemical nomenclature of the carotenoids. Science 79 488 90 PearlsteinRM( 1982) Chlorophyll singletexcitons. In Govindjee (ed) Photosynthesis. Vol I, Energy Conversion by Plants and Bacteria, pp 293-330. Academic Press, New York Perrin F (1926) Polarisation de la lumiere de fluorescence. Vie moyenne des molecules dans I etat excitb. J Physique 7 390-401... 

Many carotenoids have trivial names. However all carotenoids have been named semisystematically based on lUPAC-IUB nomenclature (lUPAC Commission on Nomenclatme of Organic Chemistry and the lUPAC-IUB Commission on Biochemical Nomenclature, 1975 Weedon and Moss, 1995). The structure of the end groups and carbon numberings of carotenoids within photosynthetic bacteria are illustrated in Fig. 1. A list of these names and the structures of all known naturally occurring carotenoids, and references giving data for each compound... 

Fig. I. Structure of the end groups and carbon numberings of carotenoids within photosynthetic bacteria based on lUPAC-IUP nomenclature (1975).

Most of the carotenoids have a trivial name which is often derived from its natural origin and which gives no information on the structure. Therefore a semi-systematic nomenclature has been developed, which has been approved by the International Union of Pure and Applied Chemistry and the International Union of Biochemistry [33] and which is accepted by Chemical Abstracts for official documentation. 

---