US3887603A - Menthol-release compounds - Google Patents

Menthol-release compounds Download PDF

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Publication number
US3887603A
US3887603A US384048A US38404873A US3887603A US 3887603 A US3887603 A US 3887603A US 384048 A US384048 A US 384048A US 38404873 A US38404873 A US 38404873A US 3887603 A US3887603 A US 3887603A
Authority
US
United States
Prior art keywords
menthol
menthyl
column
read
carbonate
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 - Lifetime
Application number
US384048A
Other languages
English (en)
Inventor
Jr Eric G S Rundberg
Jr William R Johnson
Harvey J Grubbs
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Philip Morris USA Inc
Original Assignee
Philip Morris USA Inc
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Philip Morris USA Inc filed Critical Philip Morris USA Inc
Priority to US384048A priority Critical patent/US3887603A/en
Priority to CA203,842A priority patent/CA1051453A/en
Priority to AU70895/74A priority patent/AU486017B2/en
Priority to NL7409553A priority patent/NL7409553A/xx
Priority to GB3117874A priority patent/GB1444295A/en
Priority to JP49080829A priority patent/JPS5230509B2/ja
Priority to DE2436472A priority patent/DE2436472B2/de
Priority to SU742052277A priority patent/SU650481A3/ru
Priority to CH1048974A priority patent/CH593635A5/xx
Priority to US05/559,574 priority patent/US4002179A/en
Application granted granted Critical
Publication of US3887603A publication Critical patent/US3887603A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A24—TOBACCO; CIGARS; CIGARETTES; SIMULATED SMOKING DEVICES; SMOKERS' REQUISITES
    • A24B—MANUFACTURE OR PREPARATION OF TOBACCO FOR SMOKING OR CHEWING; TOBACCO; SNUFF
    • A24B15/00—Chemical features or treatment of tobacco; Tobacco substitutes, e.g. in liquid form
    • A24B15/18—Treatment of tobacco products or tobacco substitutes
    • A24B15/28—Treatment of tobacco products or tobacco substitutes by chemical substances
    • A24B15/30—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances
    • A24B15/34—Treatment of tobacco products or tobacco substitutes by chemical substances by organic substances containing a carbocyclic ring other than a six-membered aromatic ring

Definitions

  • the present polymeric, menthol-release agents may vary greatly in molecular weight.
  • the number of monomeric units may range from 2 to 100 yielding molecular weights of from about 550 to 30,000. All such polymers are useful within the scope of this invention, however, it is preferred that polymerization be controlled through modification of the catalyst concentration, temperature, time of reaction, etc. in order to obtain reaction products having from about 6 to about 40 monomeric units or molecular weights of from about 1600 to about 12,000.
  • Theidistilled 8116, 120 mole was added Via a Syringe to the product showed a yield of 77 percent and possessed a cold, stirred solution over a period of 10 minutes. An boilingpoint in the range 67 80C at 20 mm which is evolution Of butane was noted during the addition. The the and pressure given cologne and Clerc lemon yellow solution was then stirred at room temper- Soc hi France, 195 5 836 f hi compound 1R ature for 2 hours. Because the gas evolution had not d NMR d h d a pure product ceased, the solution was warmed to about C and 35 Carbonate held there for 45 minutes.
  • Fraction 4 subjected to NMR analysis showed a 45 to 50 percent content of the mixed menthyl methylphenylbutenyl carbonate. Its odor was light and pleasant but non-menthol-like. On heating it gave a menthol odor.

Landscapes

  • Health & Medical Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Toxicology (AREA)
  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Fats And Perfumes (AREA)
  • Manufacture Of Tobacco Products (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
US384048A 1973-07-30 1973-07-30 Menthol-release compounds Expired - Lifetime US3887603A (en)

Priority Applications (10)

Application Number Priority Date Filing Date Title
US384048A US3887603A (en) 1973-07-30 1973-07-30 Menthol-release compounds
CA203,842A CA1051453A (en) 1973-07-30 1974-07-02 Menthol-release compounds
AU70895/74A AU486017B2 (en) 1973-07-30 1974-07-05 Menthol-release compounds
GB3117874A GB1444295A (en) 1973-07-30 1974-07-15 Menthol-release compounds
NL7409553A NL7409553A (nl) 1973-07-30 1974-07-15 Menthol ontwikkelende stoffen.
JP49080829A JPS5230509B2 (enExample) 1973-07-30 1974-07-16
DE2436472A DE2436472B2 (de) 1973-07-30 1974-07-29 Kohlensäure-alkenyl-menthylester-Oligomere und -Polymere sowie diese enthaltendes Tabakerzeugnis
SU742052277A SU650481A3 (ru) 1973-07-30 1974-07-29 Способ получени полимерного соединени ,выдел ющего ментол
CH1048974A CH593635A5 (enExample) 1973-07-30 1974-07-30
US05/559,574 US4002179A (en) 1973-07-30 1975-03-18 Smoking compositions incorporating a menthol-release agent

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US384048A US3887603A (en) 1973-07-30 1973-07-30 Menthol-release compounds

Related Child Applications (1)

Application Number Title Priority Date Filing Date
US05/559,574 Division US4002179A (en) 1973-07-30 1975-03-18 Smoking compositions incorporating a menthol-release agent

Publications (1)

Publication Number Publication Date
US3887603A true US3887603A (en) 1975-06-03

Family

ID=23515813

Family Applications (1)

Application Number Title Priority Date Filing Date
US384048A Expired - Lifetime US3887603A (en) 1973-07-30 1973-07-30 Menthol-release compounds

Country Status (8)

Country Link
US (1) US3887603A (enExample)
JP (1) JPS5230509B2 (enExample)
CA (1) CA1051453A (enExample)
CH (1) CH593635A5 (enExample)
DE (1) DE2436472B2 (enExample)
GB (1) GB1444295A (enExample)
NL (1) NL7409553A (enExample)
SU (1) SU650481A3 (enExample)

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4119106A (en) * 1975-10-22 1978-10-10 Philip Morris, Incorporated Flavorant-release resin compositions
US4125484A (en) * 1976-02-27 1978-11-14 Shell Oil Company Tertiary alcohols
US4912253A (en) * 1988-06-06 1990-03-27 Shin-Etsu Chemical Co., Ltd. Method for the preparation of an unsaturated alcohol or ester thereof
US5098886A (en) * 1991-03-17 1992-03-24 Narula Anubhav P S Substituted and unsubstituted alkyl cyclohexylmenthyl and cyclohexenylmethyl carbonates and perfumery uses thereof
US20030192562A1 (en) * 2000-11-06 2003-10-16 Nobukazu Higashi Tobacco odor deodorizing perfume composition, tobacco odor deodorant, cigarette low in sidestream smoke odor, and tobacco package
US12178901B2 (en) 2019-06-04 2024-12-31 Conopco, Inc. Polymer and a topical composition comprising the polymer

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS53160566U (enExample) * 1977-05-23 1978-12-15
US8632792B2 (en) * 2008-04-01 2014-01-21 Takasago International Corporation Cooling sensation agent composition and sensory stimulation agent composition
TWI850852B (zh) * 2021-11-18 2024-08-01 南韓商韓國煙草人參股份有限公司 包括新型香味劑的吸煙製品
KR102726020B1 (ko) * 2021-11-18 2024-11-06 주식회사 케이티앤지 신규한 향미제, 향미제 조성물 및 이를 포함하는 제품

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3419543A (en) * 1964-10-01 1968-12-31 Liggett & Myers Inc Carbonate esters of flavorants

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3419543A (en) * 1964-10-01 1968-12-31 Liggett & Myers Inc Carbonate esters of flavorants

Cited By (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4119106A (en) * 1975-10-22 1978-10-10 Philip Morris, Incorporated Flavorant-release resin compositions
US4127601A (en) * 1975-10-22 1978-11-28 Philip Morris, Incorporated α-Substituted vinyl menthyl carbonates
US4125484A (en) * 1976-02-27 1978-11-14 Shell Oil Company Tertiary alcohols
US4912253A (en) * 1988-06-06 1990-03-27 Shin-Etsu Chemical Co., Ltd. Method for the preparation of an unsaturated alcohol or ester thereof
US5098886A (en) * 1991-03-17 1992-03-24 Narula Anubhav P S Substituted and unsubstituted alkyl cyclohexylmenthyl and cyclohexenylmethyl carbonates and perfumery uses thereof
US20030192562A1 (en) * 2000-11-06 2003-10-16 Nobukazu Higashi Tobacco odor deodorizing perfume composition, tobacco odor deodorant, cigarette low in sidestream smoke odor, and tobacco package
US7481891B2 (en) * 2000-11-06 2009-01-27 Japan Tobacco Inc. Cigarette wrapper consisting of mandarin orange essential oil
US12178901B2 (en) 2019-06-04 2024-12-31 Conopco, Inc. Polymer and a topical composition comprising the polymer

Also Published As

Publication number Publication date
SU650481A3 (ru) 1979-02-28
JPS5039789A (enExample) 1975-04-12
CH593635A5 (enExample) 1977-12-15
NL7409553A (nl) 1975-02-03
JPS5230509B2 (enExample) 1977-08-09
DE2436472C3 (enExample) 1980-08-14
AU7089574A (en) 1976-01-08
CA1051453A (en) 1979-03-27
DE2436472A1 (de) 1975-02-27
DE2436472B2 (de) 1979-11-29
GB1444295A (en) 1976-07-28

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