Asaronic acid

When the aldehyde is heated on the water-bath with 25 per cent, hydrochloric acid, it yields a triphenylmethane derivative, nonamethoxy-triphenylmethane, a body consisting of snow-white crystals, melting at 184 5°. The action of concentrated nitric acid upon the solution in glacial acetic acid of this triphenylmethane derivative gives rise to 1, 2, 5-trimethoxy-4-nitrobenzene (melting at 130°). With bromine, nonamethoxytriphenylmethane combines, with separation of a molecule of trimethoxy bromobenzene, into a tribromo additive compound of hexamethoxy diphenylmethane, a deep violet-blue body. The 1, 2, 5-tri-methoxy-4-bromobenzene (melting at 54 5°) may be obtained more readily from asaronic acid. 

By oxidation asarone yields asarylic aldehyde, CgH2(CHO)(OCH3)g, melting at 114°, and finally asarylic acid, CgH2(COOH)(OCH3)3, melting at 144°. This acid is, of course, identical with trimethoxy-benzoic acid. 

Add a saturated solution of 40 g Na nitrite to 10 g asarone in 90 ml ether. Add dropwise over four hours 75 ml 20% sulfuric acid with stirring. Let stand eight hours filter and wash precipitate with water, ether, ethanol, and dry. Dissolve 10 g precipitate in 60 ml 8% K... 

Asarone Sd EO 23 pj. pQ Qg%DC090 Ascorbic acid, dehydro Rt 2 C244 Ascorbic acid Rt 2093 Aspartic acid pH iei Astragalin Sd ... 

Acorns calamus L. var. angustatus Besser A. gramineus Ait. A. tatarinowii L. Chang Pu (Sweet flag) (leaf, root) Acoric acid, beta-asarone, yellow bitter aromatic volatile oil, alpha-pinene, d-camphene, calamene, calamenol, calamenone.50,357-450 Anticonvulsant, analgesic, aphrodisiac, carminative, contraceptive, dessicant, diaphoretic. 

Daucus carota L. subsp. sative Hoffm. Nan He Chi (Carrot) (whole plant) Carotenes, lycopene, phytofluere, umbelliferone, alpha-pinene, camphene, myrcene, daucol, alpha-phellandrene, bisabolene, luteolin-7-glucoside, daucine, pyrrolidine, geraniol, citronellol, carotol, citral, caryophyllene, p-cymene, asarone, daucosterol, petroselinic acid.48 For chronic dysentery, worms, carminative, diuretic, emmenagogue, lower blood sugar, prevent cancer, diabetes, dyspepsia and gout. 

N.A. Acoric acid, asarone, linalool, palmitic acid, methylamine, saponin, mucilage, sesquiterpenes.99 100 103 105 Used as a panacea. It is antibacterial, antifungal, antiseptic, antiamebic, antiprotozoal, a vermifuge. Treat digestive upset, fevers. 

Methylesculetol-6,7-dinicotinate (32) is useful as an antiinflammatory and vasodilator oflow toxicity (101). The synthesis of asarone [5555-15-1] (2,4,5-trimethoxy-l-propenylbenzene), which is used as a tranquilizer, has been patented (102). It occurs in calamus root, Acorns calamus L.y and is a chemosterilant for insects (103). 6,7-Dihydroxycoumarin-4-methylsulfonic acid and its salts are useful in the treatment of capillary permeability and fragility and for protecting oxidizable metabolites and drugs against biooxidation (104). Certain chromones derived from hydroxyhydroquinone, eg (33), and its salts, esters, and amides are valuable in the prophylactic treatment of asthma (105) (see Antiasthmatic agents). 2-Methoxy-6-multiprenyl-l,4-benzoquinones are intermediates in the microbiological synthesis of coenzyme Q compounds (106). 

PROP Extract of Acorns calamus L., (Fam. Araceae). Containing asarone, eugenol esters of acetic and heptylic acids. Volatile oil. Yellow to yellowish-brown liquid (viscid) aromatic odor, bitter taste. D 0.960-0.9707 20°/20°. Very sidy sol in water misc with ale. Keep well closed, cool, and protected from light. 

C12H1406 terephthalic acid diethylene glycol ester 959-26-2 112.00 1 3940 2 24248 C12H1603 a-asarone 2883-98-9 22. To 2... 

Safrole (oxidation to the corresponding acids) appeared to be the chief constituent methyl eugenol was also present, and a small quantity of methyl iso-eugenol. Fraction 130-145° was optically active, and showed evidence of the presence of a sesquiterpene, whilst the highest fraction solidified on cooling, and proved to be asarone, melting point 62-63°. 

Now with the asarone floating on top of the nitrite, 75-ml of a 20%-by- weight solution of sulfuric acid in water is added slowly from a dropping funnel over the period of 4-5 hours. The artiele... 

The Essential Oils reports that the best general method for making pseudonitrosites is to first dissolve the asarone in petroleum ether, hexane, or even mineral spirits, and then add a concentrated aqueous solution of sodium nitrite. Then after cooling the mixture, acid is slowly introduced, and the whole mixture shaken. The batch is then allowed to stand in the cold, and the crystals filtered out later. With the pseudonitrosite thusly obtained, it s time to move on to the next stage of the reaction scheme, that of producing the nitroalkene B-nitro asarone. Put 10 grams of the pseudonitrosite into any suitable flask which can be... 

The benzaldehyde by-product is the starting material that Dr. Shulgin uses in his synthesis. If you really want this material, the better way to make it directly from asarone is with chromic acid. See Die Atherischen Ole 3" Edition, Vol. I, page 618. Then nitroethane is condensed with the asarone aldehyde to five the nitroalkene produced in this step. Nitroethane is now on the Chemical Diversion Reporting list, so I would skip that procedure unless the nitroethane is pretty handy. 

Phytochemistry Wild carrot seeds contained up to 2.5 % essential oils, which consisted of 17 substances including 1-a-pinene, myrcene, bergamotene, (3-bisabolene, caratol and asarone. Besides essential oil, the seeds contained flavonoids, coumarins, steroidal compounds and fatty oil. The roots also contain essential oils, which consisted of asarone, caratol, bisabolene and 5-9 % carotene. Large amounts of pyrrolidine and daucene were found in essential oils extracted from the herb. In the herb and flowers flavonoids, coumarins, anthocyanins, as well as large amounts of carotenoids, vitamins in the groups B and C, pantothenic acid, anthocyanidin, essential oils, umbelUferone and sugars were found (Ganunerman et al. 1990). 

Fig. 106. Separation of methoxyphenylpropane derivatives (4 (xg of each) on a silica gel G layer, using benzene. S-chamber 10 cm run, lasting 35 min spray reagent molybdophosphoric acid solution (No. 168). T Desaga test mixture 1 safrole 2 methylchavicol S myristicin 4 apiole 5 eugenol methyl ether 6 asarone 7 tetra-methoxyallylbenzene 8 elemol 9 catechol G mixture (2 [xg of each)...

Substances which should not be added as such to food include (in alphabetical order) agaric acid, aloin, capsaicin, coumarin, hypericine, P-asarone, estragole, hydrogen cyanide, menthofu-ran, methyleugenol, pulegone, safrole, quassin, safrole, teucrin A, a-thujone and P-thujone. Table 11.5 lists the plant materials that contain these natural toxic substances. Examples of maximum... 

---