Table 1419

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Microbiological Oxidation, Reduction, and Another Reaction Patterns of Monoterpenoids by Euglena gracilis Z

Microbiological Oxidation

Oxidation of alcohols Oxidation of primary alcohols to aldehydes and acids Oxidation of secondary alcohols to ketones

Oxidation of aldehydes to acids

Hydroxylation

Oxidation of olefins

Hydroxylation of nonallylic carbon Hydroxylation of allylic carbon Formation of epoxides and oxides Formation of diols Formation of triols

Lactonization

Microbiological

Reduction of aldehydes Reduction of terpene aldehydes to to alcohols terpene alcohols

Reduction of aromatic and related aldehydes to alcohols Reduction of aliphatic aldehydes to alcohols

Reduction of ketones to Reduction of saturated ketones alcohols

Reduction of a,b-unsaturated ketones Hydrogenation of olefins Hydrogenation of olefin conjugated with carbonyl group

Hydrogenation of olefin not conjugated with a carbonyl group

(-)-trans-Carveol (81a'), (+)-ci's-carveol (81b), (+)-isoborneol (36b) *Diastereo- and enantioselective dehydrogenation is observed in carveol, borneol, and isoborneol

Myrtenal (6), myrtanal, (-)-perillaldehyde (78), trans- and cis-1,2-dihydroperillaldehydes (261a and 261b), (-)-phellandral (64), trans- and cis-tetrahydroperillaldehydes, cuminaldehyde (193), (+)- and (-)-citronellal (261 and 261') *Acids were obtained as minor products

(+)-and (—)-Neodihydrocarveol (102a' and a), (—)- and (+)-dihydrocarveol (102b' and b), (+)- and (—)-isodihydrocarveol (102c' and c), (+)- and (—)-neoisodihydrocarveol (102d' and d)

Reduction

Myrtenal (6), myrtanal, (—)-perillaldehyde (78), trans- and cis-1,2-dihydroperillaldehydes (261a and 261b), phellandral (64), trans- and cis-1,2-dihydroperillaldehydes (261a and 261b), trans- and cis-tetrahydroperillaldehydes, cuminaldehyde (193), citral (275 and 276), (+)- (261) and (—)-citronellal (261')

(+)-Dihydrocarvone (101a'), (-)-isodihydrocarvone (101b), (+)-carvomenthone (48a'), (-)-isocarvomenthone (48b), (+)-dihydrocarvone-8,9-epoxides (97a'), (+)-isodihydrocarvone-8,9-epoxides (97b'), (-)-dihydrocarvone-8,9-epoxides (97a)

(-)-Carvone (93'), (+)-carvone (93), (-)-carvotanacetone (47'), (+)-carvotanacetone (47), (-)-carvone-8,9-epoxides (96'), (+)-carvone-8,9-epoxides (96)

TABLE 14.19 (continued)

Microbiological Oxidation, Reduction, and Another Reaction Patterns of Monoterpenoids by Euglena gracilis Z

Hydrolysis

Hydrolysis Hydrolysis of ester (+)-trans- and cis-Carveyl acetates (108a and b),

(—)-cis-carveyl acetate (108b'), (—)-cis-carveyl propionate, geranyl acetate (270)

Hydration

Hydration Hydration of C=C bond in (+)-Neodihydrocarveol (102a'), (—)-dihydrocarveol isopropenyl group to tertiary (102b'), (+)-isodihydrocarveol (102c'), alcohol (+)-neoisodihydrocarveol (102d')

(—)-neodihydrocarveol (102a), (+)-dihydrocarveol (102b), (—)-isodihydrocarveol (102c), (—)-neoisodihydrocarveol (102d), trans- and cis-shisools (75a and 75b)

Isomerization

Isomerization Geraniol (271), nerol (272)

9-hydroxyfenchone; 17, fenchone-9-al; 18, fenchone-9-oic acid; 19, fenchoquinone; 20, 2-hydroxy-fenchone; 21, 2,3-fencholide; 22, 1,2-fencholide; 23, verbenol; 24, verbenone; 25, 7-hydroxyver-benone; 26, 7-hydroxyverbenone; 27, verbanone-4-al; 28, thujone; 29, thujoyl alcohol; 30, 1-hydroxythujone; 31, 1,3-dihydroxythujone; 32, pinyl cation; 33, 1-p-menthene-8-cation; 34, a-ter-pineol; 35, bornyl cation; 36, borneol; 37, camphor; 38, a-pinene epoxide; 39, isonovalal; 40, nova-lal; 41, 2-hydroxypinyl cation; 42, 6-hydroxy-1-p-menthene-8-cation; 43, trans-sobrerol; 44, 8-hydroxycarvotanacetone; (carvonehydrate); 45, 8-hydraocarvomenthone; 46, 1-p-menthen-2-ol; 47, carvotanacetone; 48, carvomenthone; 49, carvomenthol; 50, 8-hydroxycarvomenthol; 51, 5-hy-droxycarvotanacetone; 52, 5-hydroxycarvomenthone; 53, 1-hydroxycarvomenthone; 54, p-men-thane-1,2-diol; 55, p-menthane-2,9-diol; 56, 2,3-lactone; 57, diepoxide; 58, 8,9-epoxy-1-p-menthanol; 59, 1-p-menthene-4-cation; 60, terpine hydrate; 61, oleuropeic acid (8-hydroxy perillic acid); 62,

1-p-menthene; 63, phellandrol; 64, phellandral; 65, phellandric acid; 66, 7-hydroxy-p-menthane; 67,

2-(4-methyl-3-cyclohexenylidene)-propionic acid; 68, limonene; 69, limonene-1,2-epoxide; 70, 1-p-menthene-9-oic acid; 71, limonene-1,2-diol; 72, 1-hydroxy-8-p-menthene-2-one; 73, 1-hydroxy-p-menth-2,8-diene; 74, perillyl alcohol; 75, shisool; 76, shisool-8,9-epoxide; 77, perillyl alcohol-8,9-epoxide; 78, perillandehyde; 79, 1-p-menthene-8,9-diol; 80, 4-hydroxy-p-menth-1,8-diene (4-terpineol); 81, carveol; 82, perillic acid; 83, 4,9-dihydroxy-1-p-menthene-7-oic acid; 84,

2-hydroxy-8-p-menthen-7-oic acid; 85, 2-oxo-8-p-menthen-7-oic acid; 86, b -isopropyl pimelic acid; 87, isopropenylglutaric acid; 88, isobutenoic acid; 89, isobutyric acid; 90, 1-p-menthene-8,9-diol; 91, carveol-8,9-epoxide; 92, bottrospicatol; 93, carvone; 94, 5-hydroxycarveol; 95, 1-p-menthene-6,9-diol; 96, carvone-8,9-epoxide; 97, dihydrocarvone-8,9-epoxide; 98, 5-hydroxycarvone; 99, 5-hydroxydihydrocarvone; 100, 5-hydroxydihydrocarveol; 101, dihydrocarvone; 102, dihydrocar-veol; 103, dihydrocarveol-8,9-epoxide; 104, p-menthane-2,8,9-triol; 105, dihydrobottrospicatol; 106, 10-hydroxydihydrocarvone; 107, 10-hydroxydihydrocarveol; 108, carveyl acetate and carveyl propionate; 109, 8,9-epoxydihydrocarveyl acetate; 110, isopiperitenol; 111, isopiperitenone; 112, piperitenone; 113, 7-hydroxyisopiperitenone; 114, 10-hydroxyisopiperitenone; 115, 4-hydroxyisopi-peritenone; 116, 5-hydroxyisopiperitenone; 117, 5-hydroxypiperitenone; 118, 7-hydroxypiperitenone; 119, pulegone; 120, 8,9-dehydromenthenone; 121, 8-hydroxy menthenone; 122, 1,8-cineole; 123,

3-hydroxy1,8-cineole; 124, 3-oxo-1,8-cineole; 125, 2-hydroxy-1,8-cineole; 126, 2-oxo-1,8-cineole;

127, 9-hydroxy-1,8-cineole; 128, lactone (R)-5,5-dimethyl-4-(3'-oxobutyl)-4,5-dihydrofuran-2-(3H)-one; 129, p-hydroxytoluene; 130, 1,8-cineole-2-malonyl ester; 131, 1,4-cineole; 132,

2-hydroxy-1,4-cineole; 133, 3-hydroxy-1,4-cineole; 134, 8-hydroxy-1,4-cineole; 135, 9-hydroxy-1,

4-cineole; 136, 1,4-cineole-2-malonyl ester; 137, menthol; 138, 1-hydroxymenthol; 139, 6-hydroxy-menthol; 140, 2-hydroxymenthol; 141, 4-hydroxymenthol; 142, 8-hydroxymenthol; 143, 7-hydroxy-menthol; 144, 9-hydroxymenthol; 145, 7,8-dihydroxymenthol; 146, 1,8-dihydroxymenthol; 147,

3-p-menthene; 148, menthenone; 149, menthone; 150, 1-hydroxymenthone; 151, 7-hydroxymen-thone; 152, 3,7-dimethyl-6-hydroxyoctanoic acid; 153, 3,7-dimethyl-6-oxoactanoic acid; 154,

2-methyl-2,5-oxidoheptenoic acid; 155, menthone-1,2-diol; 156, piperitone; 157, 8-hydroxypiperi-tone; 158, 6-hydroxypiperitone; 159, 9-hydroxypiperitone; 160, piperitone-7-al; 161, 7-hydroxypip-eritone; 162, piperitone-7-oic acid; 163, menthone-7-al; 164, menthone-7-oic acid; 165, 7-carboxylmenthol; 166, piperitone oxide; 167, 4-hydroxypiperitone; 168, piperitenone oxide; 169,

1-hydroxypulegone; 170, 2,3-seco-p-menthylacetone-3-en-1-ol; 171, 2-methyl-5-isopropyl-2,5-hexadienoic acid; 172, 2,5,6-trimethyl-2,4-heptadienoic acid; 173, 2,5,6-trimethyl-3-heptenoic acid; 174, 2,5,6-trimethyl-2-heptenoic acid; 175, 3-hydroxy-2,5,6-trimethyl-3-heptanoic acid; 176, 3-oxo-2,5,6-trimethyl-3-heptanoic acid; 177, 3,4-dimethylvaleric acid; 178, p-cymene; 179, thymol; 180, 6-hydroxythymol 181, 6-hydroxymenthenone, 6-hydroxy-4-p-menthen-3-one; 182, 3-hydroxy-thymo1,4-quinol; 183, 2-hydroxythymoquionone; 184, 2,4-dimethyl-6-oxo-3,7-dimethyl-2,4-octa-dienoic acid; 185, 2,4,6-trioxo-3,7-dimethyl octanoic acid; 186, 2-oxobutanoic acid; 187, acetic acid; 188, 8-hydroxy-p-cymene; 189, 9-hydroxy-p-cymene; 190, 2-(4-methylphenyl)-propanoic acid; 191, carvacrol; 192, cumin alcohol; 193, p-cumin aldehyde; 194, cumic acid; 195, ds-2,3-dihydroxy-2,

3-dihydro-p-cumic acid; 196, 3-hydroxycumic acid; 197, 2,3-dihydroxy-p-cumic acid; 198,

2-hydroxy-6-oxo-7-methyl-2,4-octadien-1,3-dioic acid; 199, 2-methyl-6-hydroxy-6-carboxy-7-octene; 201, 4-methyl-2-oxopentanoic acid; 202, carvacrol methyl ether; 203, 7-hydroxycarvacrol methyl ether; 204, 8-hydroxyperillyl alcohol; 205, 8-hydroxyperillaldehyde; 206, linalool; 207, linalyl-6-cation; 208, linalyl-8-cation; 209, 6-hydroxymethyl linalool; 210, linalool-6-al; 211, 2-methyl-6-hydroxy-6-carboxy-2,7-octadiene; 212, 2-methyl-6-hydroxy-7-octen-6-oic acid; 213, phellandric acid-8-cation; 214, 2,3-epoxylinalool; 215, 5-methyl-5-vinyltetrahydro-2-furanol; 216,

5-methyl-5-vinyltetrahydro-2-furanone; 217, 2,2,6-trimethyl-3-hydroxy-6-vinyltetrahydropyrane; 218, malonyl ester; 219, 1-hydroxylinalool (3,7-dimethyl-1,6-octadiene-8-ol); 220, 2,6-dimethyl-

6-hydroxy-trans-2,7-octadienoic acid; 221, 4-methyl-trans-3,5-hexadienoic acid; 222, 4-methyl-trans-3,5-hexadienoic acid; 223, 4-methyl-trans-2-hexenoic acid; 224, isobutyric acid; 225, 9-hydroxycamphor; 226, bornyl acetate; 228, 6-hydroxycamphor; 229, 6-oxocamphor; 230,

4-carboxymethyl-2,3,3-trimethylcyclopentanone; 231, 4-carboxymethyl-3,5,5-trimethyltetrahydro-2-pyrone; 232, isohydroxycamphoric acid; 233, isoketocamphoric acid; 234, 3,4,4-trimethyl-5-oxo-trans-2-hexenoic acid; 235, 5-hydroxycamphor; 236, 5-oxocamphor; 237, 238, 6-hydroxy-1, 2-campholide; 239, 6-oxo-1,2-campholide; 240, 5-carboxymethyl-3,4,4-trimethyl-2-cyclopentenone; 241, 6-car-boxymethyl-4,5,5-trimethyl-5,6-dihydro-2-pyrone; 242, 5-hydroxy-3,4,4-trimethyl-2-heptene-1,7-dioic acid; 243, 3-hydroxycamphor; 244, camphorquinone; 245, 2-hydroxyepicamphor; 246, 2-hydroxy-p-menthan-7-oic acid; 247, 2-oxo-p-menthan-7-oic acid; 248, 3-isopropylheptane-1,7-dioic acid; 249, 3-isopropylpentane-1,5-dioic acid; 250, 4-methyl-3-oxopentanoic acid; 251, methyl-isopropyl ketone; 252, p-menthane; 253, 1-hydroxy-p-menthane; 254, p-menthane-1,9-diol; 255, p-menthane-1,7-diol; 256, 1-hydroxy-p-menthene-7-al; 257, 1-hydroxy-p-menthene-7-oic acid; 258, citronellol; 259, dihydrocitronellol; 260, 2,8-dihydroxy-2,6-dimethyl octane; 261, citronellal; 262, citronellic acid; 263, pulegol; 264, 7-hydroyxmethyl-6-octene-3-ol; 265, 3,7-dimethyl-6-octane-1,8-diol; 266, 3,7-dimethyloctane-1,8-diol; 267, isopulegol; 268, 6,7-epoxycitronellol; 269, citronellyl acetate; 270, geranyl acetate; 271, geraniol; 272, nerol 273, nerol-6,7-epoxide; 274, 6,7-epoxygeran-iol; 275, neral; 276, geranial; 277, neric acid; 278, geranic acid; 279, 2,6-dimethyl-8-hydroxy-7-oxo-2-octene; 280, 6-methyl-5-heptenoic acid; 281, 7-methyl-3-carboxymethyl-2,6-octadiene-1-oic acid; 282, 7-methyl-3-hydroxy-3-carboxymethyl-6-octen-1-oic acid; 283, 7-methyl-3-oxo-6-octenoic acid; 284, 6-methyl-5-heptenoic acid; 284, 4-methyl-3-heptenoic acid; 285, 4-methyl-3-pentenoic acid; 286, 3-methyl-2-butenoic acid; 287, 3-hydroxymethyl-2,6-octadiene-1-ol; 288, 3-formyl-2,6-

octadiene-1-ol; 289, 3-carboxy-2,6-octadiene-1-ol; 290, 3-(4-methyl-3-pentenyl)-3-butenolide; 291, 7-hydroxymethyl-3-methyl-2,6-octadien-1-ol; 292, 3,7-dimethyl-2,3-dihydroxy-6-octen-1-ol; 293, 3,7-dimethyl-2-oxo-6-octene-1,3-diol; 294, 6-methyl-5-hepten-2-one; 295, 6-methyl-7-hydroxy-5-heptene-2-one; 296, 2-methyl-g-butyrolactone; 297, 6-methyl-5-heptenoic acid; 298, 6-methyl-5-hepten-2-ol; 299, 7-methyl-3-oxo-6-octanoic acid; 300, 3,7-dimethyl-2,6-octadiene-1,8-diol; 301, isopulegyl acetate; 302, myrcene; 303, 2-methyl-6-methylene-7-octene-2,3-diol; 304, 6-methylene-

7-octene-2,3-diol; 305, myrcenol; 306, ocimene; 307, myrcene-3,(10)-epoxide; 308, myrcene-3,(10)-glycol; 309, (-)-citronellene; 309', (+)-citronellene; 310, (3tf)-3,7-dimethyl-6-octene-1,2-diol; 310', (3S)-3,7-dimethyl-6-octene-1,2-diol; 311, (£>3,7-dimethyl-5-octene-1,7-diol; 312, trans-rose oxide; 313, cis-rose oxide; 314, (2Z,5£>3,7-dimethyl-2,5-octadiene-1,7-diol; 315, (Z)-3,7-dimethyl-2,7-octadiene-1,6-diol; 316, (2£,6Z)-2,6-dimethyl-2,6-octadiene-1,8-diol; 317, a cyclization product; 318, (2E,5E)-3,7-dimethyl-2,5-octadiene-1,7-diol; 319, (E)-3,7-dimethyl-2,7-octadiene-1,6-diol; 320,

8-hydroxynerol; 321, 10-hydroxynerol; 322, 1-hydroxy-3,7-dimethyl-2£',6£,-octadienal; 323, 1-hydroxy-3,7-dimethyl-2£,6£-octadienoic acid; 324, 3,9-epoxy-p-menth-1-ene; 325, tetrahydrolinalool; 326,

3.7-dimethyloctane-3,5-diol; 327, 3,7-dimethyloctane-3,7-diol; 328, 3,7-dimethyl-octane-3,8-diol; 329, dihydromyrcenol; 330, 1,2-epoxydihydromyrcenol; 331, 3b-hydroxydihydromyrcerol; 332, dihydromyrcenyl acetate; 333, 1,2-dihydroxydihydromyrcenyl acetate; 334, (+)-p-menthane-1-b,2a,8-triol; 335, a-pinene-1,2-epoxide; 336, 3-carene; 337, 3-carene-1,2-epoxide; 338, (1R)-trans-isolimonene; 338, (1R,4R)-p-menth-2-ene-8,9-diol; 339, (1R,4R)-p-menth-2-ene-8,9-diol; 340, a-Terpinene; 341, a-terpinene-7-oic acid; 342, (-)-terpinen-4-ol; 343, _p-menthane-1,2,4-triol; 344, g-terpinene; 345, g-terpinene-7-oic acid; 346, terpinolene; 347, (1R)-8-hydroxy-3-p-menthen-2-one; 348, (1R)-1,8-dihydroxy-3-p-menthen-2-one; 349, 6b -hydroxyfenchol; 350, 5b-hydroxyfen-chol (a,5b,b,5a); 351, terpinolene-1,2-trans-diol; 352, terpinolene-4,8-diol; 353, terpinolene-9-ol; 354, terpinolene-10-ol; 355, a-phellandrene; 356, a-phellandrene-7-oic acid; 357, terpinolene-7-oic acid; 358, thymoquinone; 359, 1,2-dihydroperillaldehyde; 360, 1,2-dihydroperillic acid; 361, 8-hy-droxy-1,2-dihydroperillyl alcohol; 362, tetrahydroperillaldehyde (a trans, b cis); 363, tetrahydroper-illic acid (a trans, b cis); 364, (-)-menthol monoglucoside; 365, (+)-menthol diglucoside; 366, (+)-isopulegol; 367, 7-hydroxy-(+)-isopulegol; 368, 10-hydroxy-(+)-isopulegol; 369, 1,2-epoxy- a-terpineol; 370, bornane-2,8-diol; 371, p-menthane-1a ,2b,4b-triol; 372, 1-p-menthene-4p,6-diol; 373, 1-p-menthene-4a,7-diol; 374, (+)-bottrospicatal; 375, 1-p-menthene-2p,8,9-triol; 376, (-)-peril-lyl alcohol monoglucoside; 377, (-)-perillyl alcohol diglucoside; 378, 4a-hydroxy-(-)-isodihydro-carvone; 379, 2-methyl-2-cyclohexenone; 380, 2-cyclohexenone; 381, 3-methyl-2-cyclohexenone; 382, 2-methylcyclohexanone; 383, 2-methylcyclohexanol (a, trans b, cis); 384, 4-hydroxycarvone; 385, 2-ethyl-2-cyclohexenone; 386, 2-ethylcyclohexenone (a1R) (b1S); 387, 1-hydroxypulegone; 388, 5-hydroxypulegone; 389, 8-hydroxymenthone; 390, 10-hydroxy-(-)-carvone; 391, 1,5,5-trim-ethylcyclopentane-1,4-dicarboxylic acid; 392, 4b-hydroxy-(-)-menthone; 393, 1a,4b-dihydroxy-(-)-menthone; 394, 7-hydroxy-9-carboxymenthone; 395, 7-hydroxy-1,8-cineole; 396, methyl ester of 2a-hydroxy-1,8-cineole; 397, ethyl ester of 2a-hydroxy-1,8-cineole; 398, n-propyl ester of 2a-hy-droxy-1,8-cineole; 399, n-butyl ester of 2a-hydroxy-1,8-cineole; 400, isopropyl ester of 2a-hydroxy-

1.8-cineole; 401, tertiary butyl ester of 2a-hydroxy-1,8-cineole; 402, methylisopropyl ester of 2a-hydroxy-1,8-cineole; 403, methyl tertiary butyl ester of 2a-hydroxy-1,8-cineole; 404, 2a-hy-droxy-1,8-cineole monoglucoside (404 and 404'); 405, 2a-hydroxy-1,8-cineole diglucoside; 406, p-menthane-1,4-diol; 407, 1-p-menthene-4p,6-diol; 408, (-)-pinane-2a ,3a-diol; 409, (-)-6b -hy-droxypinene; 410, (-)-4a ,5-dihydroxypinene; 411, (-)-4a-hydroxypinen-6-one; 412, 6b,7-dihy-droxyfenchol; 413, 3-oxo-pinane; 414, 2a-hydroxy-3-pinanone; 415, 2a, 5-dihydroxy-3-pinanone; 416, 2a ,10-dihydroxy-3-pinanone; 417, trans-3-pinanol; 418, pinane-2a,3a-diol; 419, pinane-2a, 3a, 5-triol; 420, isopinocampheol (3-pinanol); 421, pinane-1,3a-diol; 422, pinane-3a,5-diol; 423, pinane-3b,9-diol; 424, pinane-3b,4b,-diol; 425, 426, pinane-3a,4b-diol; 427, pinane-3a,9-diol; 428, pinane-3a,6-diol; 429, p-menthane-2a ,9-diol; 430, 2-methyl-3a-hydroxy-1-hydroxyisopropyl cyclohexane propane; 431, 5-hydroxy-3-pinanone; 432, 2a-methyl,3-(2-methyl-2-hydroxypropyl)-cyclopenta-1b-ol; 433, 3-acetoxy-2a-pinanol; 434, 8-hydroxy- a-pinene;435, 436, myrtanoic acid; 437, camphene; 438, camphene gylcol; 439, (+)-3-carene; 440, m-mentha-4,6-dien-8-ol; 441, m-cymen-8-ol; 442, 3-carene-9-ol; 443, 3-carene-9-carboxylic acid; 444, 3-caren-10-ol-9-carboxylic acid; 445, 3-carene-9,10-dicarboxylic acid; 446, (-)-cis-carane; 447, dicarboxylic acid of (-)-cis-carane; 448, (-)-6ß -hydroxypinene; 449, (-)-4a,5-dihydroxypinene; 450, (-)-4a-hydroxypinen-6-one; 451, 10-hydroxyverbenol; 452, (-)-nopol; 453, 7-hydroxymethyl-1-p-menthen-8-ol; 454,

3-oxonopol; 455, nopol benzyl ether; 456, 4-oxonopl-2',4'-dihydroxybenzyl ether; 457, 7-hydroxym-ethyl-1-p-menthen-8-ol benzyl ether; 458, piperitenol; 459, thymol methyl ether; 460, 7-hydroxy-thymol methyl ether; 461, 9-hydroxythymol methyl ether; 462, 1,8-cineol-9-oic acid; 463,

4-hydroxyphellandric acid; 464, 4-hydroxydihydrophellandric acid; 465, (+)-8-hydroxyfenchol; 466, (-)-9-hydroxyfenchol; 467, (+)-10-hydroxyfenchol, 468, 4a-hydroxy-6-oxo-a-pinene; 469, dihydro-linalyl acetate; 470, 3-hydroxycarvacrol; 471, 9-hydroxycarvacrol; 472, carvacrol-9-oic acid; 473, 8,9-dehydrocarvacrol; 474, 8-hydroxycarvacrol; 475, 7-hydroxycarvacrol; 476, carvacrol-7-oic acid; 477, 8,9-dihydroxycarvacrol; 478, 7,9-dihydroxycarvacrol methyl ether; 479, 7-hydroxythymol; 480, 9-hydroxythymol; 481, thymol-7-oic acid; 482, 7,9-dihydroxythymol; 483, thymol-9-oic acid; 484, (1R,2R,3S,4S,5R)-3,4-pinanediol.

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