Calendic acid

New oilseed crops, currently studied as potential sources of specialty fatty acids, include Crambe abyssinica for erucic acid, Limnanthes alba for very long-chain fatty acids, Dimorphotheca pluvialis for dimor-phecolic acid, Lesquerella fendleri for les-querolic acid, Calendula officinalis for calendic acid, and Euphorbia lagascae and various Vernonia species for vernolic acid.194 The lowest cost sources (inedible fats and oils and palm oil fractions) are likely most likely to be exhausted first as world trade in industrial applications grows. Cornstarch is becoming a major feedstock for plastics production. This may compete with potential oil uses, but also will increase production of com oil. 

Oils containing Cjg polyene acids Calendula officinalis seed oil. Calendula oil (from marigold) is of interest because it contains about 58% of calendic acid (8fl0fl2c-18 3). This unusual acid is an isomer of a-eleostearic (9cllfl3f-18 3) present in tung oil, and calendula oil should also be a good drying oil. The presence of linoleic acid (30%) will add to the unsaturated nature of this oil (131-133). 

A mixture of calendic acid methyl ester 1 (3 mmol, 1.50 g) and maleic anhydride (5 mmol, 0.49 g) was heated for 2h at 150 °C under nitrogen. The reaction was followed by thin-layer chromatography [petroleum ether-diethyl ether (7 3), Rf 1=0.60, Rf 3=0.23], Purification of product 3 was achieved by column chromatography [silica gel using petroleum ether/diethyl ether (7 3) and petroleum ether/ethyl acetate (1 1) as eluent]. Fractions containing product 3 were collected and the solvent was removed in vacuo. Compound 3 was recrystallized from petroleum ether/diethyl ether (4 1). 

The introduction of novel FA through plant genetic modifications has allowed the production of oils with unique characteristics valuable in industrial processes. An example is the introduction of calendic acid (8, 10, 12 all cis— 18 3) in a proportion of... 

Cahoon, E.B. K.G. Ripp S.E. Hall A.J. Kinney. Formation of conjugated delta 8, delta 10 double bonds by delta 12-oleic acid desaturase related enzymes biosynthetic origin of calendic acid./. Biol Chem. 2001,276, 2637-2643. 

Calendula, also known as Pot Marigold, has historically been grown as an ornamental and medicinal plant. Its seed oil contains up to 60% calendic acid an (8t,lot, 12c-18 3) co-6 trienoic acid synthesized in the plant from linoleate by a A12-oleate desaturase ... 

A thermal ene-reaction of unsaturated fatty acids with maleic anhydride produces branched triacids. As an example, the Diels-Alder reaction of conjugated triene fatty acids, that is calendic acid and maleic anhydride, yields a branched triacid product with high regioselectivity and stereoselectivity (Fig. 3.13). 

Calcium stearoyl lactylate, 229,233 Calea urticaefolia, 5 Calendic acid, 11 Calendula officinalis, 11,19 Californian sardine oils, 133 Calvatia gigantea, 153 Camellia sasanqua, 93 Camphor oil, 52 Canbra oil, see Rapeseed oil Candida albicans, 490 Candida species, 19,151-54,478 Candlenut oil, 52, 56,101 Cannabis sativa, 68 Canola oil, see Rapeseed oil Capelin oil, 130,132 Capillary GLC, 273 Capric acid, 1,174,179 see also Decanoic acid Caproic acid, 1,174 see also Hexanoic acid Caprylic acid, 1,174 see also Octanoic acid Carboxylic acids, polymorphism, 343 Carboxyl transferase, 485 Carcass quality of farm animals, 557 Cardiolipin, 138,156 see also Diphosphatidylglycerol Cardiovascular disease, 531,533 Carnitine, role in /S-oxidation, 494 Carotenoids, 38,154,163,397,413,446 Carthamin yellow, see Safflower Carthamus tinctorius, 84 see also Safflower Cary a species, 97... 

Figure 1. Diels-Alder reaction of calendic acid methylester and maleic anhydride and X-ray structure analysis of the product.

The pot marigold Calendula officinalis L calendula, produces an oil containing 59-65% calendic acid (Fig. 11.11.4) (Eberle et al., 2014). As an oil containing a high proportion of conjugated fatty acid, it can be used in place... 

Fritsche, K., Hornung, E., Peitzsch, N., Renz, A., Feussner, I., 1999. Isolation and characterizahon of a calendic acid producing (8, ll)-linoleoyl desaturase. FEBS Lett. 462, 249-253. 

Although calendula (Calendula officinalis) is predominantly used as an ornamental plant, the plants accumulate calendic acid (octadeca-8 10 12-trienoic acid), which can be used as a drying agent in paints, varnishes, and plastics (Beerentrup and Robbelen, 1987). In vitro regeneration ( 6911 et al., 2004 Leal et al 2009 Victorio et al., 2012) and cell suspension cultures (Grzelak and Janiszowska, 2002 Legha et al., 2012) have been reported for calendula. 

Syn. Calendic Acid tmns,trans,cis-S,10,12-Octa-decatrienoic Acid CIS 3 (A 8,10,12)... 

---