Organic compounds -- part of the class 532-570 series – Organic compounds – Oxygen containing
Reexamination Certificate
2001-10-24
2002-12-10
Shippen, Michael L. (Department: 1621)
Organic compounds -- part of the class 532-570 series
Organic compounds
Oxygen containing
C568S878000, C568S909500
Reexamination Certificate
active
06492567
ABSTRACT:
FIELD OF THE INVENTION
The present invention relates to a dihydrotagetone alcohol and to a method for the preparation thereof from from
Tagetes minuta
oil. More particularly the present invention relates to the preparation of dihydrotagetone methyl alcohol (3,5,7 trimethyl 1-ene, 5-octanol) and dihydrotagetone benzyl alcohol (3,7-dimethyl 5-benzyl, 1-ene, 5-octanol) by chemical transformation of dihydrotagetone present in essential oil of
Tagetes minuta.
BACKGROUND OF THE INVENTION
Dihydrotagetone (3,7-dimethyl, 5-one, 1-octene) find application as perfumery and flavouring material. The synthesised molecules also find application as perfumery and flavour products or as an ingredient of perfumery and flavour products. Dihydrotagetone, dihydrotagetone methyl alcohol and dihydrotagetone benzyl alcohol are also useful in the pharmaceutical industry apart from the flavour and perfumery industries.
Derivatives of the above like acetates, epoxides, peroxides, acids, amides, halides, ethers and oximes etc. also result in products for perfumery, flavour and pharmaceutical industries.
Tagetes is a genus of herbs, commonly known as MARIGOLD, originally a native of Mexico and other warmer parts of America has now naturalised elsewhere in the tropics and sub-tropics. Several species have been introduced in India. Some of them are
Tagetes patula, Tagetes erecta, Tagetes minuta, Tagetes lucida
and
Tagetes tenuifolia.
The flower heads are used for garlands. Many Tagetes species yield strongly aromatic essential oils, all of which are known as Tagetes oil. The oil is obtained from the aerial parts of the plant by steam distillation or by extracting in petroleum- ether or benzene. Prolonged distillation spoils the aroma. The leaves, especially the tender ones and flower heads are rich in oil.
Tagetes minuta
Linn. syn.
Tagetes glandulifera
Schrank (family- Compositae) is a highly aromatic annual, 1-2 m tall, native to South America, has naturalised near the waste places and on dry embankments in the North-West Himalayas between altitudes of 1250 and 2500 m.
Among all the Tagetes species grown in India,
Tagetes minuta
appears to give the highest yield of the essential oil with maximum carbonyl content, calculated as tagetone. Reference may be made to Villeirs F. J., Garbers C. F and Lasnvie R. N., 1971, synthesis of Tagetones and their occurrence in oil of
Tagetes minuta, Phytochemistry,
10, 1359. Reference may also be made to Lawrence B. M., 1992, progress in essential oils,
Perf & Flav,
17, 131-132. Another reference may be made to Singh B., Sood R. P and Singh V. 1992, chemical composition of Tagetes minuta L. from Himachal Pradesh (India),
J., Essent. Oil Res.
4, 525.
OBJECTS OF THE INVENTION
The main object of the present invention is the chemical modification of dihydrotagetone into two new perfumery and flavouring molecules.
Another object of the present invention is to provide easy and convenient method for enrichment of monoterpene and ketones in
Tagetes minuta
oil by solvent-solvent partitioning.
Still another object of the present invention is to provide methodology for isolation of dihydrotagetone (3,7-dimethyl, 5-one, 1-octene) in 100% purity having characteristic fresh, sweet, fruity and flowery odour.
Another object of the present invention is to provide a starting material for synthesis of a new perfumery and flavour molecule (3,5,7 trimethyl 1-ene, 5-octanol) in 99% yield, having minty, spicy, fresh and fruity odour.
Yet another object of the present invention is to provide starting material for synthesis of a new perfumery and flavour molecule (3,7-dimethyl 5-benzyl, 1-ene, 5-octanol) in 75% yield with sweet, flowery, aromatic like odour.
REFERENCES:
patent: 2838576 (1958-06-01), Normant
patent: 4482762 (1984-11-01), Kaiser
Joshi Virendra Prasad
Kaul Vijay Kumar
Singh Bikram
Council or Scientific and Industrial Research
Nixon & Vanderhye P.C.
Shippen Michael L.
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