Dihydrocarveol 7-Dihydrocarvone

Carvestrene, or i-sylvestrene, was first prepared by Baeyer from carvone, the ketone characteristic of oil of caraway. This body, when reduced with sodium and alcohol yields dihydrocarveol, which, on oxidation is converted into dihydrocarvone. The formulae of these three bodies are as follows —... 

On oxidation with chromic acid in acetic acid solution, dihydrocarveol yields dihydrocarvone, which has a specific gravity 0 928 at 19°, and refractive index 1-47174. The dihydrocarvone from Zae o-dihydro-carveol is dextro-rotatory, and -vice versa. Its oxime melts at 88° to 89° for the optically active variety, and at 115° to 116° for the optically inactive form. 

By reduction carvone fixes 2 atoms of hydrogen on to the ketonic group, and 2 atoms in the nucleus, with the formation of dihydrocarveol, CijHjgO, whose corresponding ketone, dihydrocarvone, Cj Hj O, exists in small quantities in caraway oil. 

Dihydrocarvone, Cj Hj O, is found to a small extent in oil of caraway, and can be prepared by the oxidation of dihydrocarveol by chromic acid in acetic acid solution. The ketone has the constitution —... 

Reduction of 0,/3-enones. NaBH4 forms a nearly homogeneous solution in pyridine at 25°. This solution reduces /-carvone (1) at 25° (12 hours) mainly to the dihydrocarveols 2. A minor product is 3. Jones oxidation of the mixture gives dihydrocarvone (4).1 This method was first reported by Kupfer.2... 

Cizkova et al. (2000) studied the direct dependence of sprouting on residual carvone and its biodegradation products in tubers. S-carvone was converted into dihydrocarveol and dihydrocarvone especially in easily accessible tissues of sprouts, peels and half tubers. Sensory analyses confirmed that S-carvone treatment of stored tubers does not influence taste, odour or colour of cooked potatoes. 

Figure 9. Seeds of caraway 1 - oc-pinene, 2 - sabinene, 3 - P-myrcene, 4 - limonene, 5 - y-terpinene, 6 - dihydrocarvon, 7 - dihydrocarveol, 8 - carvone.

Diethyl malonate Diethyl sebacate Diethyl succinate Diethyl tartrate 2,5-Diethyltetrahydrofuran Dihydrocarveol d-Dihydrocarvone DihydrocarvyI acetate Dihydrocoumarin Dihydro-p-ionone... 

Eight kinds of 8 hydroj dihydrocarveols (50a-d and 50a -d 8-p-menthane-2,8-diols) were obtained from carvone (93 and 93 ), dihydrocarvones (101a b and lOla -b ), and dihydrocarveols (102a d, 102a d ) by E. gracilis Z. as shown in Figure 19.99 (Noma et al., 1993). 

Group 1 Carvone (93), dihydrocarvones (101), dihydrocarveol (102), dihydrocarveol-8,9-ep-oxide (103), dihydrobottrospicatols (105), 5-hydroxydihydrocarveols (100)... 

Dihydrocarveol, T5 Dihydrocarvone, T5 Dihydrocorynantheane, K2 Dihydrocoumarilic acid, Y1 Dihydroguaiols, T25 Dihydroguaiaretic acid dimethyl ether, A31... 

The constituents recognised in caraway oil are carvone, d-limonene, dihydrocarvone, carveol, and dihydrocarveol, and a base having a nai-cotic odour which has not been investigated. 

---