Naphthalene-1-acetic acid

Naphthalene Acetic Acid and Naphthalene Acetamide. Naphthalene acetic acid [26445-01-2] (38) is historicaHy one of the first plant growth regulators. Reports concerning its activity in crops and plants have been a subject in much of the eady Hterature (57). Consequently, it has been used as a starting matedal for other compounds, eg, vide infra Sevin. Naphthaleneacetamide [31093-43-3] (39) has been used as a standard matedal to evaluate abscission pnor to 1953 and its effect on apple drop was reported in 1953 (58). The substance is used as an internal standard in the abscission bioassay (59). 

Naphthalene acetic acid is used to thin apple and pear blossoms and to control apple and pear preharvest drop (10). It also is used to induce flowering in pineapple, but conversely inhibits sprouting in potatoes, sweet potatoes, and turnips (Brassica rapd) (23). It also is used to promote rooting in... 

Trinitro-5-hydroxy-l-acetoxy-naphthalene, acetic acid-[2,6,8-trinitro-5-hydroxy-1 -naphthyl-ester], [2,6,8-trinitro-5-hyd roxy-1 -naphthyl] -acetate). (O2N)3C10H3(OCOCH3).OH, mw 337.22, N 12.46%, OB to C02 -87.78%, yellow needles... 

Galun, E. (1959). Effects of gibberellic acid and naphthalene-acetic acid on sex expression and some morphological characters in the cucumber plant. Phyton (Buenos Aires) 13,1-8. 

NAA,Naphthalene acetic acid ABA.Abscisic acid BAL,1,2-Dimercap-topropane PAL,Phenylalanine ammonia-lyase. 

As far back as the 1940 s, chemicals that we now classify as plant growth regulators were used experimentally to root cuttings and to promote flowering in pineapple. The first important commercial application of a plant growth regulator was in the 1940 s, when naphthalene acetic acid was applied, as it still is, to prevent the preharvest drop of apples. 

In this context, we recently discovered close correlations between auxin-induced ethylene synthesis, massive accumulations of ABA in root md even more in shoot tissue and inhibition of their growth. This phenomenon, which has been reported for the first time, was demonstrated for auxin herbicides from different chemical classes (Figure 1), such as quinmerac, quinclorac, MCPA, naphthalene acetic acid, dicamba and picloram, and lAA at high concentration, in a variety of dicot species, including members of the Sola-naceae, Umbelliferae, Fabaceae, Scrophulariaceae and Brassicaceae [35, 39, 40]. ABA accumulation and concomitant epinastic effects and reduced shoot growth were also... 

In D. stramonium there exists a close relationship between PMT activity, the morphological state of cultures and the biosynthesis of hyoscyamine. In fact, it was found that when de-differentiation was induced with a mixture of kinetin, 2,4-dichlorophenoxyacetic acid and a-naphthalene-acetic acid, the PMT activity and hyoscyamine biosynthesis were lost [127]. Furthermore, it seems that PMT... 

Fig. la. Structures of plant hormones (a) Auxins Indole-3-acetic acid (lAA) Indoleacetonitrile (IAN) Phenylacetic acid (PAA) 2,4-dichlorophenoxyacetic acid (2,4-D) a-naphthalene acetic acid (NAA). 

Heteroarylacetie aeid analogues 2. Arylacetic acid analogues 3. Arylpropionie aeid analogues 4. Naphthalene acetic acid analogues... 

The reeent intensive quest for non-steroid anti-inflammatory drugs and arylacetic acids in particular offer a brighter seope that the naphthalene acetic acid analogues might turn out to be the leading compounds of an extensive series of promising clinical agents. Example Naproxen. 

It is a naphthalene acetic acid structural analogue available commercially as the acid and its sodium salt and is sold OTC. The drug is fairly comparable to aspirin both in the management and control of disease symptoms. Nevertheless, it has relatively lesser frequency and severity of nervous system together with milder GI-effects. 

Naproxen derived from naphthalene acetic acid analogue proved to be the leading compoimd of an extensive series of promising elinieal agents. Deseribe its synthesis from 6-methoxy naphthalene. 

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