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GB1580184A - Perfumery compositions - Google Patents

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Publication number
GB1580184A
GB1580184A GB8655/76A GB865576A GB1580184A GB 1580184 A GB1580184 A GB 1580184A GB 8655/76 A GB8655/76 A GB 8655/76A GB 865576 A GB865576 A GB 865576A GB 1580184 A GB1580184 A GB 1580184A
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United Kingdom
Prior art keywords
oil
compounds
composition according
formula
acetate
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
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GB8655/76A
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Bush Boake Allen Ltd
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Bush Boake Allen Ltd
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Filing date
Publication date
Application filed by Bush Boake Allen Ltd filed Critical Bush Boake Allen Ltd
Priority to GB8655/76A priority Critical patent/GB1580184A/en
Publication of GB1580184A publication Critical patent/GB1580184A/en
Expired legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C35/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring
    • C07C35/22—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring polycyclic, at least one hydroxy group bound to a condensed ring system
    • C07C35/37—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring polycyclic, at least one hydroxy group bound to a condensed ring system with a hydroxy group on a condensed system having three rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
    • C07C29/03—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by addition of hydroxy groups to unsaturated carbon-to-carbon bonds, e.g. with the aid of H2O2
    • C07C29/04—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by addition of hydroxy groups to unsaturated carbon-to-carbon bonds, e.g. with the aid of H2O2 by hydration of carbon-to-carbon double bonds
    • C07C29/05—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by addition of hydroxy groups to unsaturated carbon-to-carbon bonds, e.g. with the aid of H2O2 by hydration of carbon-to-carbon double bonds with formation of absorption products in mineral acids and their hydrolysis
    • C07C29/06—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by addition of hydroxy groups to unsaturated carbon-to-carbon bonds, e.g. with the aid of H2O2 by hydration of carbon-to-carbon double bonds with formation of absorption products in mineral acids and their hydrolysis the acid being sulfuric acid
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/385—Saturated compounds containing a keto group being part of a ring
    • C07C49/417—Saturated compounds containing a keto group being part of a ring polycyclic
    • C07C49/423—Saturated compounds containing a keto group being part of a ring polycyclic a keto group being part of a condensed ring system
    • C07C49/453—Saturated compounds containing a keto group being part of a ring polycyclic a keto group being part of a condensed ring system having three rings
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B9/00—Essential oils; Perfumes
    • C11B9/0042—Essential oils; Perfumes compounds containing condensed hydrocarbon rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2603/00—Systems containing at least three condensed rings
    • C07C2603/93—Spiro compounds
    • C07C2603/95—Spiro compounds containing "not free" spiro atoms
    • C07C2603/96—Spiro compounds containing "not free" spiro atoms containing at least one ring with less than six members
    • C07C2603/97—Spiro compounds containing "not free" spiro atoms containing at least one ring with less than six members containing five-membered rings

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Environmental & Geological Engineering (AREA)
  • General Life Sciences & Earth Sciences (AREA)
  • Geochemistry & Mineralogy (AREA)
  • Geology (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Fats And Perfumes (AREA)

Description

(54) PERFUMERY COMPOSITIONS (71) We, BUSH BOAKE ALLEN LIMITED, a British Company of Blackhorse Lane, Walthamstow, London E17 5QP, do hereby declare the invention for which we pray that a Patent may be granted to us and the method by which it is to be performed to be particularly described in and by the following statement:- This invention relates to certain organic chemicals and mixtures of organic chemicals which find application as odoriferous ingredients of perfumery compositions of the type wherein a number of odoriferous ingredients of synthetic or natural origin are mixed together to form a perfumery concentrate.
From one aspect the invention provides a perfumery composition comprising a plurality of odoriferous ingredients and one or more compounds having the formula I or II.
Such compounds may consist of individual isomers of compounds having either of the above formulae or mixtures of the aforesaid isomers.
The carbon skeleton of these compounds will be recognised as that of the known sesquiterpene clovan, and for the purposes of this disclosure the alcohol having the formula I will be referred to as clovanol and the ketone of formula II will be referred to as clovanone.
Clovan may be obtained by reduction of the monoethylenically unsaturated hydrocarbon clovene which is a constituent of clove oil. More usually compounds having this carbon skeleton are obtained as one of the products of the acid catalysed hydration of the known sesquiterpene caryophyllene. These sesquiterpenes have been the subject of a good deal of interest among organic chemists who were interested in evaluating their molecular structure. In the course of such a study the compounds clovanol and clovanone were synthesised by D.H.R. Barton and A.
Nickon as was reported in the Journal of the Chemical Society 1954 page 4665.
However no indication of any potential value of these, or any of the many other derivatives of clovan which were synthesised, was given. More recently it has been reported in West German Offenlegungschrift 2440024 that the formate ester of clovanol is a useful ingredient of perfumery and flavouring compositions. Suprisingly we have now discovered that clovanol and clovanone also possess interesting oderiferous properties which makes them valuable ingredients of a compounded perfumery composition. In contrast to the formate esters which are reported as having a fine woody type of odour the corresponding alcohol clovanol has a woody earthy type of odour with a distinct patchouli, cedarwood note while clovanone has a similar type of odour in which the dry woody character is considerably enhanced.
Compounds whose odours exhibit a woody note are of particular and increasing value in the perfumery industry as ingredients of perfumery compositions designed to impart an attractive perfume to toiletry articles for male use. Clovanol and clovanone blend well with other ingredients of such perfumery compositions and can be used to impart a woody note thereto having the patchouli, cedarwodd overtones unique to these compounds.
Clovanol and clovanone may be employed as a minor or a major ingredient of such compositions dependant upon the particular type of composition desired. In general the compounds clovanol and/or clovanone will constitute from 0.1 to 80 parts by weight, preferably from 1.0 to 20.0 parts by weight of such a composition. The perfumery concentrates of this invention may find use as such or after dilution but more usually they are added in small proportions to other materials such as space sprays or to soap, cosmetic or deoderant compositions or to substrates such as fibre, fabric or paper products in order to provide them with agreeable olfactory properties. Such concentrates are products of commerce and they may comprise a simple or complex mixture of individual perfumery concentrates.
The novel perfumery compositions of the invention may be compounded according to recognised techniques of perfumery employing known odoriferous perfumery ingredients such as those described in the standard text books of the art e.g. "Soap, Perfumery and Cosmetics" by W.A.
Poucher. 7th Edition, published by Chapman and Hall (London) 1959; "Perfume and Flavour Chemicals" by S.
Arctander published by the author (Montclair) 1959 and "Perfume and Flavour Materials of Natural Origin" also by S. Arctander self-published Elizabeth New Jersey (1960). Specific odoriferous ingredients which may be blended with clovanol and/or clovanone in a compounded perfumery composition are the derivatives of 2, 6 - dimethyl - 2 - alkoxy octan - 7 ol hereinafter described as 2 - alkoxy elgenols as claimed in our British Patent No. 1414458, vetivert oil, vetiverol, vetiveryl acetate, guaiac wood oil, guaiac wood acetate, coumarin musk ketone, lauric aldehyde, benzyl acetate, lemon oil, dimethyl benzyl carbinol, dimethyl benzyl carbinyl acetate, rose absolute, jasmin absolute, ionones, iso-nonyl acetate, methyl phenyl acetate, styrallyl acetate, B phenyl ethanol, citronellol, citronellal, hydroxy citronellal, geranium oil, geraniol, linalol, nerol, lavandin oil, linalyl acetate, patchouli oil, petitgrain oil, bergamot oil, heliotropin, ethylene brassylate, undecyl aldehyde, cinnamaldehyde, benzyl salicylate, cinnamyl alcohol, clove bud oil, bay oil, nutmeg oil, pimento berry oil, terpineol, ylang oil, benzyl benzoate, sandalwood oil, clary sage oil, amyl salicylate, labdanum resin, methyl ionones, dihydro-myrcenol, orange oil, vanillin, ethylvanillin, olibanum resin, musk ambrette, rhodinol, mandarin oil, methylnonyl acetaldehyde, neroli oil cedrol, oakmoss, isovalanone, eugenol, isoeugenol, cedarwood oil, p-tert-butyl cyclohexyl acetate.
Typically the compounds of our invention are blended with at least two, usually at least five and preferably at least ten of the foregoing ingredients.
Particularly preferred ingredients for blending with clovanol or clovanone in a compounded perfumery composition are the oils of patchouli, cedar, vetiver, sandalwood, lavender, bergamot, lemon, geranium, oakmoss, clove and petitgrain and also synthetic perfumery materials such as musk ambrette, musk ketone, musk xylenes, coumarin, linalool, linalyl acetate, gerniol, citronellol, phenyl ethyl alcohol, benzyl acetate, eugenol, isoeugenol, amyl cinnamic aldehyde, hexyl cinnamic aldehyde, hydroxycitronellal, 2 alkoxyelgenols, acetyl cedrene, cedrol, cedryl acetate, vetiverol, vetiveryl acetate.
The alcohol, clovanol may conveniently be prepared trom sesquiterpene hydrocarbon caryophyllene which occurs widely as a major sesquiterpene constituent of clove oil and also as a high boiling fraction of some turpentine oils. Acid catalysed hydration of caryophyllene leads to the formation of a mixture of products which include caryophyllene alcohol i.e.
the compound having the formula
and clovanol.
The hydration may be carried out in aqueous solution in the presence of a strong acid catalyst such as a mineral acid or ptoluene sulphonic acid. Preferably however the hydration is carried out by reacting caryophyllene with an equimolar quantity of a carboxylic acid preferably a lower aliphatic carboxylic acid such as formic acid or acetic acid at a temperature of from 20 to 600 C, over a period of from 8 to 24 hours. The presence of a strong acid catalyst is essential if the reaction employing a carboxylic acid other than formic acid is to proceed at a reasonable rate. The product of such a reaction will comprise a mixture of the appropriate carboxylic acid esters of the alcohols clovanol and caryophyllene alcohol. The corresponding alcohols may of course be obtained from these esters by saponification using the conventional techniques of synthetic organic chemistry.
The use of a carboxylic acid to facilitate the hydration of caryophyllene increases the quantity of clovanol which is formed and results in the formation of correspondingly lesser quantities of unwanted hydrocarbon byproducts.
The products of the hydration may be separated using conventional techniques such as fractional distillation. However when the hydration is carried out under the preferred conditions the product consists primarily of a mixture of the esters of caryophyllene alcohol and clovanol which mixture may conveniently be saponified by the addition of an aqueous solution of a base at reflux temperature so as to produce a mixture of the two alcohols. These alcohols may also be separated by crystallisation or fractional distillation.
The ketone, clovanone, may be obtained by oxidation of clovanol. Any technique known in the art of organic chemistry for oxidising secondary alcohols such as dehydrogenation by passage over a copper catalyst or refluxing with aluminium tbutoxide in a large excess of acetone may be employed. However preferably the oxidation is achieved by addition of a mildly acidic solution of water soluble dichromate such as potassium dichromate.
In a particularly convenient synthesis these oxidation techniques may be applied to the mixture of the two alcohols produced by hydration of caryophyllene. The tertiary alcohol caryophyllene alcohol, is not susceptible to oxidation under such conditions and is left unchanged. The product of such a technique comprises a mixture of caryophyllene alcohol and clovanone from which these two constituents may be separated if this is desirable. Such separation may be achieved by crystallation or fractional distillation.
However such a separation involves a degree of inconvenience. Suprisingly we have discovered that the valuable odoriferous properties of clovanol and clovanone are exhibited, to a diminishing degree when they are admixed with caryophyllene alcohol. Since a mixture of these two compounds can be obtained by a relatively simple fractionation of the product of the reaction described above it may be convenient to employ such a mixture as an ingredient of a compounded perfumery composition directly and thus avoid using a more rigorous separation technique in order to separate the clovanol or clovanone from the caryophyllene alcohol. In fact the odours of these two chemicals are complementary and the mixtures of the two can be used in the type of compositions which have been hereinbefore described in which clovanol or clovanone find particular utility. While all such mixtures of caryophyllene alcohol with clovanol and/or clovanone may be employed as ingredients of a compounded perfumery composition in general the clovanol and/or clovanone will constitute at least 40% preferably 80% by weight of such a mixture. The value of caryophyllene alcohol in a compounded perfumery composition lies primarily in its fixative effect rather than its own individual odoriferous properties and in many compositions the presence of larger quantities of a fixative ingredient is not necessary for the optimum odoriferous effect to be achieved.
The invention is illustrated by the following Examples in which Examples 1 to 3 illustrate the preparation of the products useful according to the invention.
Example 1 204 gms of caryophyllene was placed in a suitable flask together with 250 gms of glacial acetic acid and 6.5 gms of concentrated sulphuric acid and stirred for 10 hours at a temperature of 20"C. The resulting mixture was diluted with water and the desired product mixture of esters extracted with light petroleum. The solvent was removed and the esters treated with an excess of aqueous 40% sodium hydroxide.
The product comprised an oily layer from which 110 gms of a mixture of clovanol and caryophyllene alcohol were obtained as a fraction boiling in the range 1190C--125"C at 2.0 mm pressure. The clovanol and caryophyllene alcohol were present in a weight ratio of 6:4.
Example 2 The product obtained from Example 1 was oxidised by treatment with an equimolar quantity of Jones' reagent at a temperature of 25-300C. The product was washed with a dilute aqueous solution of sodium carbonate and subsequently dried on sodium sulphate. Fractionation of the product produced a fraction boiling in the range 101 to 1050C at 1.0 mm pressure.
Example 3 The procedure of Example I was repeated using an equimolar quantity of anhydrous formic acid in place of the acetic acid. A mixture comprising clovanol and caryophyllene alcohol in a molar ratio of 1:1.
Example 4 A compounded perfumery composition as a patchouli base was made up as follows; all parts being expressed as parts by weight: Oil of Patchouli 500 Oil of Cedarwood 30 Para tertiary-butyl cyclohexanol 50 Methoxyelgenol 50 Musk Ambrette 30 Versalide 20 Isopropyl Quinoline 5 Clovol 335 Example 5 A compounded perfumery having a woody fragrance composition was made up as follows all parts expressed as parts by weight.
Oil of Bergamot 200 Oil of Lemon 70 Oil of Lime 50 Oil of Geranium 20 Oil of Lavender (French) 20 Oil of Patchouli 20 Oil of Cedarwood 20 Oil of Sandalwood 10 Oil of Galbanum 5 Oil of Clary Sage 5 Hexyl Cinnamic Aldehyde 80 V Methyl Ionone 60 Hydroxycitronellal 50 Musk Ambrette 40 Acetyl Cedrene 50 Phenyl ethyl alcohol 20 Methoxyelgenol 50 Styrallyl Acetate 10 Hedione 10 Coumarin 30 Isoeugenol 20 C,0-aldehyde 10 C12-aldehyde 10 Oakmoss absolute 30 Rose absolute (synthetic) 10 Jasmine absolute (synthetic) 10 Olibanum Resinoid 20 Opponax Resinoid 20 Clovanone 50 WHAT WE CLAIM IS: 1. A compounded perfumery composition which comprises a plurality of odoriferous ingredients and one or more compounds having the formula I or II.
2. A composition according to claim 1 wherein the compounds of formula I or II are blended with at least five other odoriferous ingredients.
3. A composition according to claim 2 wherein the compounds of formula I or II are blended with at least ten other odoriferous ingredients.
4. A composition according to any of the preceding claims wherein the compounds of formula I or II are blended with one or more odoriferous ingredients selected from the oils of patchouli, cedar, vetivert, sandalwood lavender, oakmoss, bergamot, lemon geranium, clove and petitgrain; musk ambrette, musk ketone, musk xylenes, coumarin, linalool, linalyl acetate, geraniol, citronellol, phenyl ethyl alcohol, benzyl acetate, eugenol, isoeugenol, amyl cinnamic aldehyde, hexyl cinnamic aldehyde, hydroxycitronellal, 2alkoxyelgenols, acetyl cedrene, cedrol, cedryl acetate, vetiverol and vetiveryl acetate.
5. A composition according to any of the preceding claims wherein the compounds of the formula I and/or II constitute from 0.1 to 80 parts by weight of the composition.
6. A composition according to claim 5 wherein the compounds of the formula I and/or II constitute from 1.0 to 20 parts by weight of the composition.
7. A composition according to any of the preceding claims which further comprises caryophyllene alcohol.
8. A composition according to any of the preceding claims which comprises a mixture of the compounds of formula I and/or II and caryophyllene alcohol, said compounds comprising at least 40% by weight of said mixture.
9. A composition according to claim 8 wherein said compounds comprise at least 80 /n by weight of said mixture.
10. A composition according to any of the preceding claims substantially as described with reference to examples 4 and 5.
**WARNING** end of DESC field may overlap start of CLMS **.

Claims (10)

**WARNING** start of CLMS field may overlap end of DESC **. as follows all parts expressed as parts by weight. Oil of Bergamot 200 Oil of Lemon 70 Oil of Lime 50 Oil of Geranium 20 Oil of Lavender (French) 20 Oil of Patchouli 20 Oil of Cedarwood 20 Oil of Sandalwood 10 Oil of Galbanum 5 Oil of Clary Sage 5 Hexyl Cinnamic Aldehyde 80 V Methyl Ionone 60 Hydroxycitronellal 50 Musk Ambrette 40 Acetyl Cedrene 50 Phenyl ethyl alcohol 20 Methoxyelgenol 50 Styrallyl Acetate 10 Hedione 10 Coumarin 30 Isoeugenol 20 C,0-aldehyde 10 C12-aldehyde 10 Oakmoss absolute 30 Rose absolute (synthetic) 10 Jasmine absolute (synthetic) 10 Olibanum Resinoid 20 Opponax Resinoid 20 Clovanone 50 WHAT WE CLAIM IS:
1. A compounded perfumery composition which comprises a plurality of odoriferous ingredients and one or more compounds having the formula I or II.
2. A composition according to claim 1 wherein the compounds of formula I or II are blended with at least five other odoriferous ingredients.
3. A composition according to claim 2 wherein the compounds of formula I or II are blended with at least ten other odoriferous ingredients.
4. A composition according to any of the preceding claims wherein the compounds of formula I or II are blended with one or more odoriferous ingredients selected from the oils of patchouli, cedar, vetivert, sandalwood lavender, oakmoss, bergamot, lemon geranium, clove and petitgrain; musk ambrette, musk ketone, musk xylenes, coumarin, linalool, linalyl acetate, geraniol, citronellol, phenyl ethyl alcohol, benzyl acetate, eugenol, isoeugenol, amyl cinnamic aldehyde, hexyl cinnamic aldehyde, hydroxycitronellal, 2alkoxyelgenols, acetyl cedrene, cedrol, cedryl acetate, vetiverol and vetiveryl acetate.
5. A composition according to any of the preceding claims wherein the compounds of the formula I and/or II constitute from 0.1 to 80 parts by weight of the composition.
6. A composition according to claim 5 wherein the compounds of the formula I and/or II constitute from 1.0 to 20 parts by weight of the composition.
7. A composition according to any of the preceding claims which further comprises caryophyllene alcohol.
8. A composition according to any of the preceding claims which comprises a mixture of the compounds of formula I and/or II and caryophyllene alcohol, said compounds comprising at least 40% by weight of said mixture.
9. A composition according to claim 8 wherein said compounds comprise at least 80 /n by weight of said mixture.
10. A composition according to any of the preceding claims substantially as described with reference to examples 4 and 5.
GB8655/76A 1977-04-12 1977-04-12 Perfumery compositions Expired GB1580184A (en)

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GB8655/76A GB1580184A (en) 1977-04-12 1977-04-12 Perfumery compositions

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GB8655/76A GB1580184A (en) 1977-04-12 1977-04-12 Perfumery compositions

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GB1580184A true GB1580184A (en) 1980-11-26

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1996008147A3 (en) * 1994-09-12 1996-11-21 Quest Int Improvements in or relating to insect repellents
WO2009087242A2 (en) 2009-04-09 2009-07-16 Symrise Gmbh & Co. Kg Compositions comprising trans-tert-butyl cyclohexanol as skin irritation-reducing agent

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1996008147A3 (en) * 1994-09-12 1996-11-21 Quest Int Improvements in or relating to insect repellents
WO2009087242A2 (en) 2009-04-09 2009-07-16 Symrise Gmbh & Co. Kg Compositions comprising trans-tert-butyl cyclohexanol as skin irritation-reducing agent

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