EP0138860A1 - 1- ad(3-methylthio)-1-oxo-butyl bd-cyclohexene methyl substitue, son procede de fabrication et son utilisation comme parfum et aromate - Google Patents

1- ad(3-methylthio)-1-oxo-butyl bd-cyclohexene methyl substitue, son procede de fabrication et son utilisation comme parfum et aromate

Info

Publication number
EP0138860A1
EP0138860A1 EP84900980A EP84900980A EP0138860A1 EP 0138860 A1 EP0138860 A1 EP 0138860A1 EP 84900980 A EP84900980 A EP 84900980A EP 84900980 A EP84900980 A EP 84900980A EP 0138860 A1 EP0138860 A1 EP 0138860A1
Authority
EP
European Patent Office
Prior art keywords
fruity
methylthio
compound
methyl
amount
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.)
Withdrawn
Application number
EP84900980A
Other languages
German (de)
English (en)
Inventor
Ernst-Joachim Brunke
Willi Rojahn
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.)
Dragoco Gerberding and Co GmbH
Original Assignee
Dragoco Gerberding and Co GmbH
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 Dragoco Gerberding and Co GmbH filed Critical Dragoco Gerberding and Co GmbH
Publication of EP0138860A1 publication Critical patent/EP0138860A1/fr
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/22—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and doubly-bound oxygen atoms bound to the same carbon skeleton
    • 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
    • C11B9/0026—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring
    • C11B9/0034—Essential oils; Perfumes compounds containing an alicyclic ring not condensed with another ring the ring containing six carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C2601/00—Systems containing only non-condensed rings
    • C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
    • C07C2601/16—Systems containing only non-condensed rings with a six-membered ring the ring being unsaturated

Definitions

  • the invention relates to the new methyl-substituted 1 - [(3-methylthio) -1-oxobutyl] cyclohexenes, the preparation thereof and use as fragrance and aroma substances.
  • ⁇ - and ß-Damascon and ß-Damascenon are more than j Natural component of essential oils or aromas has been proven; they are also synthesized and used as a fragrance and flavoring agent [review in: E. Theimer (ed.), Fragrance Chemistry, Academic Press, New York 1982].
  • DE-PS 2 808 710 (issue date September 18, 1980) describes the thiomethyl ethers which consist of ß-Damascon and ß-Damascenon have been shown. The connections and were isolated from black tobacco oil.
  • the taste characteristics the connection were called “sweet, pronounced of black tea, tobacco-like, chocolate-like, reminiscent of dried fruits, rose petals "and that of the compound as” sweet pronounced of black tea, cocoa-like, damascenon-like ".
  • the olfactory properties of were described as” flowery and of course rose oil-like "and those of” earthy, Potato-like top note, with a mint-like, tomato-like, Brussels sprouts-like shade with a woody undertone ".
  • the new compound of the Thiomethylother des ⁇ -Damascons is a double bond isomer of the compound and surprisingly has a smell of taste and taste properties that differ greatly from the olfactory properties of the ß-damascontiomethyl ether.
  • the new connection smells very strongly fresh-fruity in the direction of "tropical
  • the taste characteristics can be pronounced fruity with hints of black currant, or raspberry
  • the new thiomethyl ether was made from ⁇ -isodamascon and from ß-isodamascon [E. Klein and W. Rojahn, Tetrahedron Letters 1971, 3607] obtained by reaction with methyl mercaptan in the presence of organic bases. From the mixture of compounds and is added by adding methylmercaotane Mixture of thiomethyl ether 1 and obtained. The new ver bindings or bzu. the mixture and own strong fruity smell and taste egg properties.
  • Flavor concentrate "Williams Christ pear" a b
  • Mixture a has a typical pear aroma
  • Flavor concentrate type "Black currant" a
  • Cinnamaldehyde 1.0 Cinnamaldehyde 1.0
  • the mixture a has a balanced fruity aroma complex of the type "black currant".
  • the mixture b which contains 0.05% of the compound, has a stronger effect, emphasizes the desired note and comes very close to the natural model.
  • This blend is a standard recipe for a "Rose / Geranium” type soap perfume oil.
  • the addition of only 0.2 parts of the compounds or and and 1 causes a great charisma and natural effect.
  • Aroma blend for tobacco a b c
  • the flavor mixtures a, b and c were sprayed onto a smoking tobacco (Virginia / Burley, 1: 1) in a dosage of 0.1%.
  • the tobacco flavored with b had a much stronger smoking effect than the tobacco blend with the aroma a and showed an additional fresh, fruity note.
  • the tobacco flavored with the mixture c showed a note reminiscent of dried fruit compared to that flavored with a.
  • the compounds 1a, 1b and 1c are used individually or in a mixture in amounts of 0.1 ppm or more.
  • amounts of 0.5 to 20 ppm are preferred, these amounts always being based on the end product.
  • quantities of 0.1 to 0.2 ppm are also often sufficient, and in the perfume oil itself, that is to say in the perfume concentrate, which is then diluted into the perfume or incorporated into, for example, cosmetics or other end products, the compound is usually in an amount of 0 , 02% before.
  • a total content of 0.01% of the end product of compound 1a, lb and / or lc is rarely exceeded and is sufficient for all practical purposes.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Fats And Perfumes (AREA)
  • Seasonings (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Les thiométhyléthers 1a-c, qui sont préparés à partir d'alpha- damascone, d'alpha-isodamascone, de beta-isodamascone ou de méthylmercaptan, possédant des propriétés olfactives originelles de type fruité et peuvent être utilisés avantageusement comme composant efficace olfactif de parfums, d'articles parfumés, de produits alimentaires, de chewing-gum, de tabacs et de produits pour soins buccaux.
EP84900980A 1983-03-05 1984-03-05 1- ad(3-methylthio)-1-oxo-butyl bd-cyclohexene methyl substitue, son procede de fabrication et son utilisation comme parfum et aromate Withdrawn EP0138860A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE3307869 1983-03-05
DE19833307869 DE3307869A1 (de) 1983-03-05 1983-03-05 Methylsubstituierte 1-((3-methylthio)-1-oxo-butyl)-cyclohex-2-ene, verfahren zu deren herstellung und deren verwendung als riech- und aromastoffe

Publications (1)

Publication Number Publication Date
EP0138860A1 true EP0138860A1 (fr) 1985-05-02

Family

ID=6192637

Family Applications (1)

Application Number Title Priority Date Filing Date
EP84900980A Withdrawn EP0138860A1 (fr) 1983-03-05 1984-03-05 1- ad(3-methylthio)-1-oxo-butyl bd-cyclohexene methyl substitue, son procede de fabrication et son utilisation comme parfum et aromate

Country Status (3)

Country Link
EP (1) EP0138860A1 (fr)
DE (1) DE3307869A1 (fr)
WO (1) WO1984003508A1 (fr)

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US4659510A (en) * 1984-11-14 1987-04-21 Kuraray Company, Ltd. Trimethylcyclohexenyl compounds and aroma compositions containing the same
US9249229B2 (en) 2000-12-08 2016-02-02 Alexion Pharmaceuticals, Inc. Polypeptides and antibodies derived from chronic lymphocytic leukemia cells and uses thereof
US7408041B2 (en) 2000-12-08 2008-08-05 Alexion Pharmaceuticals, Inc. Polypeptides and antibodies derived from chronic lymphocytic leukemia cells and uses thereof
US20060057651A1 (en) 2000-12-08 2006-03-16 Bowdish Katherine S Polypeptides and antibodies derived from chronic lymphocytic leukemia cells and uses thereof
CA2436595C (fr) 2000-12-08 2011-11-08 Alexion Pharmaceuticals, Inc. Lignee cellulaire de la leucemie lymphoide chronique et son utilisation pour la production d'un anticorps
WO2002098897A2 (fr) 2001-06-01 2002-12-12 Cornell Research Foundation, Inc. Anticorps modifies diriges contre l'antigene prostatique specifique membranaire et utilisations associees
JP4694785B2 (ja) * 2001-12-13 2011-06-08 フイルメニツヒ ソシエテ アノニム 活性分子を制御放出するための化合物
US20080025913A1 (en) 2003-12-15 2008-01-31 Bowdish Katherine S Novel Anti-Dc-Sign Antibodies
US7973134B2 (en) 2004-07-07 2011-07-05 Cell Signaling Technology, Inc. Reagents for the detection of protein phosphorylation in anaplastic large cell lymphoma signaling pathways
US7935790B2 (en) 2004-10-04 2011-05-03 Cell Singaling Technology, Inc. Reagents for the detection of protein phosphorylation in T-cell receptor signaling pathways
US7807789B2 (en) 2004-12-21 2010-10-05 Cell Signaling Technology, Inc. Reagents for the detection of protein phosphorylation in EGFR-signaling pathways
EP1868647A4 (fr) 2005-03-24 2009-04-01 Millennium Pharm Inc Anticorps se liant à ov064 et leurs méthodes d'utilisation
EP1934867A2 (fr) 2005-08-31 2008-06-25 Cell Signaling Technology, Inc. Reactifs de detection de phosphorylation proteinique dans des voies de signalisation de leucemie
CN103690947A (zh) 2006-01-12 2014-04-02 阿莱克申药物公司 抗ox-2/cd200的抗体及其用途
US7939636B2 (en) 2006-08-11 2011-05-10 Cell Signaling Technology, Inc. Reagents for the detection of protein phosphorylation in c-Src signaling pathways
US20090081659A1 (en) 2007-03-07 2009-03-26 Cell Signaling Technology, Inc. Reagents for the detection of protein phosphorylation in carcinoma signaling pathways
EP1975184A3 (fr) 2007-03-26 2008-11-26 Cell Signaling Technology, Inc. Sites de phosphorylation à sérine ou thréonine
US7977462B2 (en) 2007-04-19 2011-07-12 Cell Signaling Technology, Inc. Tyrosine phosphorylation sites
EP2145902A3 (fr) 2007-04-19 2010-09-29 Peter Hornbeck Sites de phosphorylation à tyrosine et anticorps spécifiques
EP1983003A3 (fr) 2007-04-19 2009-03-11 Peter Hornbeck Sites de phosphorylation à tyrosine et anticorps spécifiques
US20090053831A1 (en) 2007-05-01 2009-02-26 Cell Signaling Technology, Inc. Tyrosine phosphorylation sites
KR20100036362A (ko) 2007-07-25 2010-04-07 알렉시온 파마슈티칼스, 인코포레이티드 자가면역 질환 치료 방법 및 조성물
US20090203043A1 (en) 2007-11-21 2009-08-13 Peter Hornbeck Protein phosphorylation by basophilic serine/threonine kinases in insulin signaling pathways
EP3023502A1 (fr) 2008-04-10 2016-05-25 Cell Signaling Technology, Inc. Compositions et procédés pour détecter des mutations egfr dans le cancer
US8829159B2 (en) 2008-04-14 2014-09-09 The General Hospital Corporation Plectin-1 targeted agents for detection and treatment of pancreatic ductal adenocarcinoma
EP2304439A4 (fr) 2008-05-29 2012-07-04 Nuclea Biotechnologies Llc Anticorps anti-phospho-akt
EP3044295B1 (fr) 2013-09-09 2018-05-02 Firmenich SA Dérivés de thioéther en tant que précurseurs pour une libération contrôlée de molécules actives
CN108139375A (zh) 2015-06-26 2018-06-08 贝斯以色列女执事医疗中心股份有限公司 靶向髓样衍生的抑制细胞中的四跨膜蛋白33(tspan33)的癌症疗法
WO2019067499A1 (fr) 2017-09-27 2019-04-04 Alexion Pharmaceuticals, Inc. Signature de biomarqueur pour la prédiction d'une réponse tumorale vis-à-vis d'une thérapie anti-cd200
US20210087267A1 (en) 2017-12-20 2021-03-25 Alexion Pharmaceuticals, Inc. Liquid formulations of anti-cd200 antibodies
WO2019126536A1 (fr) 2017-12-20 2019-06-27 Alexion Pharmaceuticals Inc. Anticorps humanisés anti-cd200 et leurs utilisations
CN115803062A (zh) 2020-06-03 2023-03-14 博泰康医药公司 滋养层细胞表面抗原2(trop-2)抗体
EP4281484A1 (fr) 2021-01-22 2023-11-29 Bionecure Therapeutics, Inc. Constructions anti-her-2/trop-2 et leurs utilisations

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4107209A (en) * 1977-03-03 1978-08-15 International Flavors & Fragrances Inc. 1-[3-(Methylthio)butyryl]-2,6,6-trimethyl-cyclohexene and the 1,3-cyclohexadiene analog
DE3228289A1 (de) * 1982-07-29 1984-02-09 Dragoco Gerberding & Co Gmbh, 3450 Holzminden 1-(1-methylthio-3-oxo-butyl)-2,6,6-trimethyl- cyclohexene und deren verwendung als riech- und aromastoff

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO8403508A1 *

Also Published As

Publication number Publication date
DE3307869A1 (de) 1984-09-06
WO1984003508A1 (fr) 1984-09-13

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PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

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Designated state(s): CH DE FR GB LI NL

STAA Information on the status of an ep patent application or granted ep patent

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18D Application deemed to be withdrawn

Effective date: 19850731

RIN1 Information on inventor provided before grant (corrected)

Inventor name: BRUNKE, ERNST-JOACHIM

Inventor name: ROJAHN, WILLI