3- Methoxy-5-methylphenol

In rat liver slices, evidence also supports the roles of QMs in mediating the toxicity of a series of 4-methylphenols.24 The potency correlates with rates of QM formation in the order 2-bromo-4-methylphenol > 4-methylphenol = DMP > TMP > 2-methoxy-4-methylphenol. None of these compounds contain two bulky ortho substituents, so as discussed earlier the corresponding QMs are expected to be highly reactive. The authors suggested that differences in the reactivities of these QMs determine their relative toxic potencies as electron-donating substituents on the ring stabilize the QM and thereby reduce its toxicity (e.g., 2-methoxy-4-methylphenol is less toxic than DMP) and conversely, electron-withdrawing substituents destabilize QMs and enhance toxicity (e.g., 2-bromo-4-methylphenol is more potent than DMP). 

Structural information on aromatic donor molecule binding was obtained initially by using H NMR relaxation measurements to give distances from the heme iron atom to protons of the bound molecule. For example, indole-3-propionic acid, a structural homologue of the plant hormone indole-3-acetic acid, was found to bind approximately 9-10 A from the heme iron atom and at a particular angle to the heme plane (234). The disadvantage of this method is that the orientation with respect to the polypeptide chain cannot be defined. Other donor molecules examined include 4-methylphenol (p-cresol) (235), 3-hydroxyphenol (resorcinol), 2-methoxy-4-methylphenol and benzhydroxamic acid (236), methyl 2-pyridyl sulfide and methylp-tolyl sulfide (237), and L-tyrosine and D-tyrosine (238). Distance constraints of between 8.4 and 12.0 A have been reported (235-238). Aromatic donor proton to heme iron distances of 6 A reported earlier for aminotriazole and 3-hydroxyphenol (resorcinol) are too short because of an inappropriate estimate of the molecular correlation time (239), a parameter required for the calculations. Distance information for a series of aromatic phenols and amines bound to Mn(III)-substituted HRP C has been published (240). 

Properties. Vanillin is a colorless crystalline solid mp 82-83 °C) with a typical vanilla odor. Because it possesses aldehyde and hydroxyl substituents, it undergoes many reactions. Additional reactions are possible due to the reactivity of the aromatic nucleus. Vanillyl alcohol and 2-methoxy-4-methylphenol are obtained by catalytic hydrogenation vanillic acid derivatives are formed after oxidation and protection of the phenolic hydroxyl group. Since vanillin is a phenol aldehyde, it is stable to autoxidation and does not undergo the Cannizzarro reaction. Numerous derivatives can be prepared by etherification or esterification of the hydroxyl group and by aldol condensation at the aldehyde group. Several of these derivatives are intermediates, for example, in the synthesis of pharmaceuticals. 

Methoxy-4-methylphenol, AN69 8-Methoxy-2-methylquinoline, AT36... 

Creosol (2-methoxy-4-methylphenol) (I), for instance, yields 14.5% methanol and 15% carbon dioxide on a mole basis. Besides these degradation products, up to 60% of the crystalline o,o -dihydroxybiphenyl derivative (6,6 -bicreosol—i.e., 2,2 -dihydroxy-3,3 -dimethoxy-5,5 -dimethylbi-phenyl-1,1 ) (II) and small amounts of a higher molecular humic-like compound could be isolated. 

Eremopetasidione (440), isolated recently from rhizomes of Petasites japonicus MAXIM, has been used in the treatment of tonsillitis, contusion and poisonous snake bites in Chinese medicine. Recently, racemic 440 was synthesized in 9 steps (30% overall yield) starting from 2-methoxy-4-methylphenol (421) (Scheme 85) . Oxidation of 421 with PhI(OAc)2 in MeOH in the presence of ethyl vinyl ketone (EVK) afforded in 96% yield a Diels-Alder adduct 441, which was converted into sUyl enolate 442 in 96% yield. This enolate further underwent Cope rearrangement to give regio- and stereoselectively the desired c -decalin 443 (70%). Further conversion of 443 to the target molecule 440 was then accomplished. 

M Holocher-Ertl, K Kratzl. Modellversuche zur Sauerstoffbleiche von Zellstoff. 4 Mitt. Zum oxidativen Abbau von Lignin Abbau von Kreosol (2-Methoxy-4-methylphenol) mit molekularem Sauerstoff, Wasserstoffperoxid und Ozon. Holsforschung 36 11-16, 1982. 

H.34) Phenol, 2-methoxy-4-methyl-, 2-methoxy-4-methylphenol, 2-methoxy-p-cresol, creosol, 4-methylguaiacol, homoguaiacol, 3-methoxy-4-hydroxytoluene, 4-hydroxy-3-methoxy-1 -methylbenzene [93-51-6) FEMA 2671... 

Methoxy-4-methyl-2-pentanone 2-Methoxy-4-methylphenol 1-Methoxynaphthalene 2-Methoxynaphthalene 2-Methoxy-1,4-naphthalenedione 4-Methoxy-1-naphthol... 

Homo-cuminic aldehyde. See p-Isopropylphenylacetaldehyde Homoguaiacol. See 2-Methoxy-4-methylphenol Homolinalool... 

Methoxy-4-methylpentan-2-one 4-Methoxy-4-methyl-2-pentanone Methoxy-4-methyl-4-pentanone-2. See 4-Methoxy-4-methylpentanone-2 2-Methoxy-4-methylphenol CAS 93-51-6 EINECS/ELINCS 202-252-9 FEMA 2671... 

Methylglyoxal. See Pyruvaldehyde 2-Methyl glyoxaline. See 2-Methyl imidazole Methylguaiacol 4-Methylguaiacol p-Methylguaiacol. See 2-Methoxy-4-methylphenol... 

Methoxy-4-methylphenol 2-Methoxy-3(5)-methylpyrazine 4-p-Methoxyphenyl-2-butanone... 

Methoxy-4-methylphenol 202-255-5 2-Phenylpropanal 202-256-0 1-Phenyl-1-propanol 202-257-6 Ethyl phenyl ketone 202-259-7 Methyl benzoate 202-261-8 Methyl nicotinate 202-268-6 Aradur 2844 Casamine 0TB o-Tolyl biguanide 202-280-1 Ablumide SDE Alkamide DS-280 Alkamide DS-280/S Amidex SE Aromide HL-21 Colamid 280 Hetamide DS Jeemide N-1918 Karamide ST-DEA Lipamide S Loramide SD Marvansoft RE-1256 Monamid 718 Nopcogen 14-S Olamida ED Onyxol 42 Protamide SA Stearamide DEA Unamide S Unamide W Upamide SD 202-281-7 Active 18... 

---