Carotenoid acids

More severe conditions, 35 ml of 35% methanolic KOH added to 10 mL extract in EtOAc and shaken for 20 min at 50°C, are necessary for the total conversion of bixin, an ester of a carotenoid acid, to norbixin in snacks. Since saponification yields the norbixin salt (K or Na, depending on the alkali) that is soluble in the aqueous phase, the pH should be decreased to 3.5 or even lower to allow extraction of the protonated norbixin by EtOAc and diethyl ether. ... 

Preparation of 7 -apo-7 -(4-carboxyphenyl)-P-carotene (14, IS) began with a Wittig reaction of trans-p-apo-8 -carotenal and 4-(carbomethoxy)benzyltri-phenylphosphonium bromide, followed by base hydrolysis (15). The carotenoid acid was converted to the acid chloride (16) with thionyl chloride. 

Finally, couphng this porphyrin quinone with the carotenoid acid chloride 16 yielded the target triad 1 in 53% yield. 

Aasen, A.J., and S. Liaaen-Jensen Fungal Carotenoids II. The Structure of the Carotenoid Acid Neurosporaxanthin. Acta Chem. Scand. 19, 1843 (1965). 

New carotenoid glycosyl esters have been obtained from galactose and maltose and the imidazolyl or 1,2,4-triazolyl derivative of the carotenoid acid in the presence of sodium hydride. 

Light and photosynthetic electron transport convert DPEs into free radicals of undetermined stmcture. The radicals produced in the presence of the bipyridinium and DPE herbicides decrease leaf chlorophyll and carotenoid content and initiate general destmction of chloroplasts with concomitant formation of short-chain hydrocarbons from polyunsaturated fatty acids (37,97). 

Isophorone usually contains 2—5% of the isomer P-isophorone [471-01-2] (3,5,5-trimethyl-3-cyclohexen-l-one). The term a-isophorone is sometimes used ia referring to the a,P-unsaturated ketone, whereas P-isophorone connotes the unconjugated derivative. P-lsophorone (bp 186°C) is lower boiling than isophorone and can be converted to isophorone by distilling at reduced pressure ia the presence of -toluenesulfonic acid (188). Isophorone can be converted to P-isophorone by treatment with adipic acid (189) or H on(Ill) acetylacetoate (190). P-lsophorone can also be prepared from 4-bromoisophorone by reduction with chromous acetate (191). P-lsophorone can be used as an iatermediate ia the synthesis of carotenoids (192). 

TSR L, TSR L is a color-specified mbber, and the light amber color is produced by selecting clones with a low carotenoid content. After collection, the field latex is preserved with a mixture of ammonia and boric acid and subsequendy treated using 0.05% sodium metabisulfite to inhibit... 

The stmcture of vitamin A [11103-57-4] and some of the important derivatives are shown in Figure 1. The parent stmcture is aH-Zra/ j -retinol [68-26-8] and its lUPAC name is (all-E)-3,7-dimethyl-9-(2,6,6-trimethyl-l-cyclohexen-l-yl)-2,4,6,8-nonatetraen-l-ol (1). The numbering system for vitamin A derivatives parallels the system used for the carotenoids. In older Hterature, vitamin A compounds are named as derivatives of trimethyl cyclohexene and the side chain is named as a substituent. For retinoic acid derivatives, the carboxyl group is denoted as C-1 and the trimethyl cyclohexane ring as a substituent on C-9. The stmctures of vitamin A and -carotene were elucidated by Karrer in 1930 and several derivatives of the vitamin were prepared by this group (5,6). In 1935, Wald isolated a substance found in the visual pigments of the eye and was able to show that this material was identical with Karrer s retinaldehyde [116-31-4] (5) (7). 

Fig. 3. Commeicially important carotenoids P-caiotene (10), canthaxanthin [514-78-3] (11), astaxanthin [472-61-7] (12), P-apo-8 -caiotenal [1107-26-2] (13), P-apo-8 -caiotenoic acid ethyl ester [1109-11-1] (14), and citranaxanthin [3604-90-8] (15).

Because of the presence of an extended polyene chain, the chemical and physical properties of the retinoids and carotenoids are dominated by this feature. Vitamin A and related substances are yellow compounds which are unstable in the presence of oxygen and light. This decay can be accelerated by heat and trace metals. Retinol is stable to base but is subject to acid-cataly2ed dehydration in the presence of dilute acids to yield anhydrovitamin A [1224-18-8] (16). Retro-vitamin A [16729-22-9] (17) is obtained by treatment of retinol in the presence of concentrated hydrobromic acid. In the case of retinoic acid and retinal, reisomerization is possible after conversion to appropriate derivatives such as the acid chloride or the hydroquinone adduct. Table 1 Hsts the physical properties of -carotene [7235-40-7] and vitamin A. 

Com endosperm oil—A reddish brown Hquid composed chiefly of glycerides, fatty acids, sitosterols, and carotenoid pigments obtained by isopropyl alcohol and hexane extraction from the gluten fraction of yellow com grain. 

It is important to note that diet is a complex mixture that contain compounds with varying activity. Chemical stimulators of colon cancer growth include bile acids, 1,2-diglycerides and prostaglandins which stem from consumption of fat. In contrast, fruits and vegetables contain substances such as carotenoids, flavonoids and fibre, which may inhibit cancer cell growth, and the risk of colon cancer appears to be mirrored by the ratio of plant sterols to cholesterol in the... 

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