DE1908756C3 - Riechstoffkomposition - Google Patents
RiechstoffkompositionInfo
- Publication number
- DE1908756C3 DE1908756C3 DE1908756A DE1908756A DE1908756C3 DE 1908756 C3 DE1908756 C3 DE 1908756C3 DE 1908756 A DE1908756 A DE 1908756A DE 1908756 A DE1908756 A DE 1908756A DE 1908756 C3 DE1908756 C3 DE 1908756C3
- Authority
- DE
- Germany
- Prior art keywords
- dimethyl
- fragrance composition
- pyran
- dihydro
- methyl
- 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
Links
- 239000000203 mixture Substances 0.000 title claims description 16
- 239000003205 fragrance Substances 0.000 title claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 4
- GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 description 10
- 239000005792 Geraniol Substances 0.000 description 5
- GLZPCOQZEFWAFX-YFHOEESVSA-N Geraniol Natural products CC(C)=CCC\C(C)=C/CO GLZPCOQZEFWAFX-YFHOEESVSA-N 0.000 description 5
- 229940113087 geraniol Drugs 0.000 description 5
- QMVPMAAFGQKVCJ-UHFFFAOYSA-N citronellol Chemical compound OCCC(C)CCC=C(C)C QMVPMAAFGQKVCJ-UHFFFAOYSA-N 0.000 description 4
- KBFFVAYZFNJXAW-UHFFFAOYSA-N 2-butyl-4,6-dimethyl-3,6-dihydro-2h-pyran Chemical compound CCCCC1CC(C)=CC(C)O1 KBFFVAYZFNJXAW-UHFFFAOYSA-N 0.000 description 3
- XPOKALKENSYQGX-UHFFFAOYSA-N 2-butyl-6-methyl-4-methylideneoxane Chemical compound CCCCC1CC(=C)CC(C)O1 XPOKALKENSYQGX-UHFFFAOYSA-N 0.000 description 3
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 3
- 241000208152 Geranium Species 0.000 description 3
- QMVPMAAFGQKVCJ-SNVBAGLBSA-N (R)-(+)-citronellol Natural products OCC[C@H](C)CCC=C(C)C QMVPMAAFGQKVCJ-SNVBAGLBSA-N 0.000 description 2
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 description 2
- OSMLMQQJZVENMX-UHFFFAOYSA-N 6-butyl-2,4-dimethyl-3,6-dihydro-2h-pyran Chemical compound CCCCC1OC(C)CC(C)=C1 OSMLMQQJZVENMX-UHFFFAOYSA-N 0.000 description 2
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 2
- 235000010254 Jasminum officinale Nutrition 0.000 description 2
- 240000005385 Jasminum sambac Species 0.000 description 2
- QUKGYYKBILRGFE-UHFFFAOYSA-N benzyl acetate Chemical compound CC(=O)OCC1=CC=CC=C1 QUKGYYKBILRGFE-UHFFFAOYSA-N 0.000 description 2
- SESFRYSPDFLNCH-UHFFFAOYSA-N benzyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-N 0.000 description 2
- JGQFVRIQXUFPAH-UHFFFAOYSA-N beta-citronellol Natural products OCCC(C)CCCC(C)=C JGQFVRIQXUFPAH-UHFFFAOYSA-N 0.000 description 2
- 235000000484 citronellol Nutrition 0.000 description 2
- FLKPEMZONWLCSK-UHFFFAOYSA-N diethyl phthalate Chemical compound CCOC(=O)C1=CC=CC=C1C(=O)OCC FLKPEMZONWLCSK-UHFFFAOYSA-N 0.000 description 2
- RRAFCDWBNXTKKO-UHFFFAOYSA-N eugenol Chemical compound COC1=CC(CC=C)=CC=C1O RRAFCDWBNXTKKO-UHFFFAOYSA-N 0.000 description 2
- ZYTMANIQRDEHIO-KXUCPTDWSA-N isopulegol Chemical compound C[C@@H]1CC[C@@H](C(C)=C)[C@H](O)C1 ZYTMANIQRDEHIO-KXUCPTDWSA-N 0.000 description 2
- CDOSHBSSFJOMGT-UHFFFAOYSA-N linalool Chemical compound CC(C)=CCCC(C)(O)C=C CDOSHBSSFJOMGT-UHFFFAOYSA-N 0.000 description 2
- UWKAYLJWKGQEPM-LBPRGKRZSA-N linalyl acetate Chemical compound CC(C)=CCC[C@](C)(C=C)OC(C)=O UWKAYLJWKGQEPM-LBPRGKRZSA-N 0.000 description 2
- NFLGAXVYCFJBMK-IUCAKERBSA-N (-)-isomenthone Chemical compound CC(C)[C@@H]1CC[C@H](C)CC1=O NFLGAXVYCFJBMK-IUCAKERBSA-N 0.000 description 1
- 239000001871 (1R,2R,5S)-5-methyl-2-prop-1-en-2-ylcyclohexan-1-ol Substances 0.000 description 1
- 239000001414 (2E)-2-(phenylmethylidene)octanal Substances 0.000 description 1
- 239000001490 (3R)-3,7-dimethylocta-1,6-dien-3-ol Substances 0.000 description 1
- YKSSSKBJDZDZTD-XVNBXDOJSA-N (E)-isoeugenyl benzyl ether Chemical compound COC1=CC(\C=C\C)=CC=C1OCC1=CC=CC=C1 YKSSSKBJDZDZTD-XVNBXDOJSA-N 0.000 description 1
- CDOSHBSSFJOMGT-JTQLQIEISA-N (R)-linalool Natural products CC(C)=CCC[C@@](C)(O)C=C CDOSHBSSFJOMGT-JTQLQIEISA-N 0.000 description 1
- MKEIDVFLAWJKMY-UHFFFAOYSA-N 1,7-dioxacycloheptadecan-8-one Chemical compound O=C1CCCCCCCCCOCCCCCO1 MKEIDVFLAWJKMY-UHFFFAOYSA-N 0.000 description 1
- QQLIGMASAVJVON-UHFFFAOYSA-N 1-naphthalen-1-ylethanone Chemical compound C1=CC=C2C(C(=O)C)=CC=CC2=C1 QQLIGMASAVJVON-UHFFFAOYSA-N 0.000 description 1
- FACFHHMQICTXFZ-UHFFFAOYSA-N 2-(2-phenylimidazo[1,2-a]pyridin-3-yl)ethanamine Chemical compound N1=C2C=CC=CN2C(CCN)=C1C1=CC=CC=C1 FACFHHMQICTXFZ-UHFFFAOYSA-N 0.000 description 1
- FLUWAIIVLCVEKF-UHFFFAOYSA-N 2-Methyl-1-phenyl-2-propanyl acetate Chemical compound CC(=O)OC(C)(C)CC1=CC=CC=C1 FLUWAIIVLCVEKF-UHFFFAOYSA-N 0.000 description 1
- 125000006020 2-methyl-1-propenyl group Chemical group 0.000 description 1
- -1 6-isobutyl-2,4-dimethyl-5,6-dihydro-2H-pyran Chemical compound 0.000 description 1
- 240000007436 Cananga odorata Species 0.000 description 1
- NPBVQXIMTZKSBA-UHFFFAOYSA-N Chavibetol Natural products COC1=CC=C(CC=C)C=C1O NPBVQXIMTZKSBA-UHFFFAOYSA-N 0.000 description 1
- WTEVQBCEXWBHNA-UHFFFAOYSA-N Citral Natural products CC(C)=CCCC(C)=CC=O WTEVQBCEXWBHNA-UHFFFAOYSA-N 0.000 description 1
- 239000004641 Diallyl-phthalate Substances 0.000 description 1
- 239000005770 Eugenol Substances 0.000 description 1
- 241001632578 Hyacinthus orientalis Species 0.000 description 1
- 244000061176 Nicotiana tabacum Species 0.000 description 1
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 1
- 244000270673 Pelargonium graveolens Species 0.000 description 1
- 235000017927 Pelargonium graveolens Nutrition 0.000 description 1
- UVMRYBDEERADNV-UHFFFAOYSA-N Pseudoeugenol Natural products COC1=CC(C(C)=C)=CC=C1O UVMRYBDEERADNV-UHFFFAOYSA-N 0.000 description 1
- 241000220317 Rosa Species 0.000 description 1
- 241000109329 Rosa xanthina Species 0.000 description 1
- 235000004789 Rosa xanthina Nutrition 0.000 description 1
- 244000297179 Syringa vulgaris Species 0.000 description 1
- 235000004338 Syringa vulgaris Nutrition 0.000 description 1
- 244000172533 Viola sororia Species 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- GUUHFMWKWLOQMM-NTCAYCPXSA-N alpha-hexylcinnamaldehyde Chemical compound CCCCCC\C(C=O)=C/C1=CC=CC=C1 GUUHFMWKWLOQMM-NTCAYCPXSA-N 0.000 description 1
- 229940072717 alpha-hexylcinnamaldehyde Drugs 0.000 description 1
- GUUHFMWKWLOQMM-UHFFFAOYSA-N alpha-n-hexylcinnamic aldehyde Natural products CCCCCCC(C=O)=CC1=CC=CC=C1 GUUHFMWKWLOQMM-UHFFFAOYSA-N 0.000 description 1
- 229940007550 benzyl acetate Drugs 0.000 description 1
- 229960002903 benzyl benzoate Drugs 0.000 description 1
- QUDWYFHPNIMBFC-UHFFFAOYSA-N bis(prop-2-enyl) benzene-1,2-dicarboxylate Chemical compound C=CCOC(=O)C1=CC=CC=C1C(=O)OCC=C QUDWYFHPNIMBFC-UHFFFAOYSA-N 0.000 description 1
- CCRCUPLGCSFEDV-UHFFFAOYSA-N cinnamic acid methyl ester Natural products COC(=O)C=CC1=CC=CC=C1 CCRCUPLGCSFEDV-UHFFFAOYSA-N 0.000 description 1
- 229940043350 citral Drugs 0.000 description 1
- 229940095104 dimethyl benzyl carbinyl acetate Drugs 0.000 description 1
- 229960002217 eugenol Drugs 0.000 description 1
- WTEVQBCEXWBHNA-JXMROGBWSA-N geranial Chemical compound CC(C)=CCC\C(C)=C\C=O WTEVQBCEXWBHNA-JXMROGBWSA-N 0.000 description 1
- 239000010648 geranium oil Substances 0.000 description 1
- 235000019717 geranium oil Nutrition 0.000 description 1
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 1
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 1
- NFLGAXVYCFJBMK-UHFFFAOYSA-N isomenthone Natural products CC(C)C1CCC(C)CC1=O NFLGAXVYCFJBMK-UHFFFAOYSA-N 0.000 description 1
- 229940095045 isopulegol Drugs 0.000 description 1
- 229930007744 linalool Natural products 0.000 description 1
- UWKAYLJWKGQEPM-UHFFFAOYSA-N linalool acetate Natural products CC(C)=CCCC(C)(C=C)OC(C)=O UWKAYLJWKGQEPM-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- CCRCUPLGCSFEDV-BQYQJAHWSA-N methyl trans-cinnamate Chemical compound COC(=O)\C=C\C1=CC=CC=C1 CCRCUPLGCSFEDV-BQYQJAHWSA-N 0.000 description 1
- 229940067137 musk ketone Drugs 0.000 description 1
- ZYTMANIQRDEHIO-UHFFFAOYSA-N neo-Isopulegol Natural products CC1CCC(C(C)=C)C(O)C1 ZYTMANIQRDEHIO-UHFFFAOYSA-N 0.000 description 1
- 101150115538 nero gene Proteins 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 150000004880 oxines Chemical class 0.000 description 1
- 230000000149 penetrating effect Effects 0.000 description 1
- 239000002304 perfume Substances 0.000 description 1
- 239000001738 pogostemon cablin oil Substances 0.000 description 1
- 239000010671 sandalwood oil Substances 0.000 description 1
Classifications
-
- 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
- C11B9/0069—Heterocyclic compounds
- C11B9/0073—Heterocyclic compounds containing only O or S as heteroatoms
- C11B9/008—Heterocyclic compounds containing only O or S as heteroatoms the hetero rings containing six atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
- C07D309/16—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C07D309/18—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member containing only hydrogen and carbon atoms in addition to the ring hetero atom
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)
- Pyrane Compounds (AREA)
- Cosmetics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
H2C"" ^CH
C C ΓΙ
/ \ / \ n-QH, O CH3
CH2
/ \ H2C CH2
H-C C-H
/ \ / \ n-QH, O CH3
Die Erfindung betrifft eine neue Riechstoffkomposition.
Durch die NL-OS 64 12 168 ist es bereits bekannt, daß
6-(2-Methyl-l-propenyl)-2,4,6-trimethyl-2H-5H-dihydropyran sowie dessen Isomere einen vorherrschenden
Rosendurft in Verbindung mit einem geringeren Geraniendurft besitzen. Aus der genannten NL-OS
ergibt sich weiter, daß Dihydropyrane nicht generell als Duftstoffe geeignet sind. So wird z. B. angegeben, daß
das 6-Isobutyl-2,4-dimethyl-5,6-dihydro-2H-pyran als Parfüm unbrauchbar ist.
Überraschenderweise wurde nun gefunden, daß sich bestimmte Pyranderivate gut als Riechstoffe eignen.
Gegenstand der Erfindung ist eine Riechstoffkomposition enthaltend eine oder mehrere Verbindungen der
Formeln
CH3 to
HC CH2
H C C-H
/ \ / \ n-QHo O CIU
CH3
C
C
/ V
H2C CH
H-C C-H
/ \ / \ n-QH, O CH3
CH,
C
C
H2C
H-C
/ N
n-QH,
/ N
n-QH,
CH2
C-H
CH3
Die Verbindungen, die einzeln und in Mischung verwendet werden können, besitzen eine sehr hervorstechende,
durchdringende grüne Geruchsnuance mit einem klaren Anflug von Geranie und können in
verschiedenen Kompositionen eingesetzt werden. So verleihen sie blumenähnlichen KomDositionen eine
natürliche, grüne Note von Geranie, Rose, Jasmin. Hyazinthe, Flieder und Veilchen. Für solche Zusammensetzungen
genügen sehr geringe Mengen von 0,1 —0^%. Höhere Dosierungen von 0,5—2% verleihen
Kompositionen eine Fougere-, Tabak-, Chypre-Note oder andere Phantasie-Noten.
Die für die erfindungsgemäße Riechstoffkomposition benötigten Verbindungen lassen sich gemäß der US-PS
24 52 977 herstellen.
Beispiel 1 Geranienölkomposition
100 g eines Gemisches aus
2,4-Dimethyl-6-n-butyl-2,3-dihydro-6H-pyran, 2,4-Dimethyl-6-n-butyl-5,6-dihydro-2H-pyran
und
2-Methyl-4-methylen-6-n-butyltetrahydropyran
(d%= 0,8585, nf = 1,4477)
40 g Dimethylsulfid, 1 %ig in Geraniol 30 g Isomenthon
450 g Geraniol
50 g Nero!
250 g Citronellol
10 g Linalool
450 g Geraniol
50 g Nero!
250 g Citronellol
10 g Linalool
30 g Eugenol, 10%ig in Geraniol 20 g Citral, 10%ig in Geraniol
20 g Isopulegol, 10%ig in Geraniol 1000 g insgesamt
20 g Isopulegol, 10%ig in Geraniol 1000 g insgesamt
Beispiel 2 Rosengeranienkomposition
15 g Benzylisoeugenol
15 g Moschusketon
15 g Moschusketon
10 g 11 -Oxahexadecanolid
10 g Dimethyl-benzyl-carbinylazetat 50 g Rhodinol 50 g Sandelholzöl (O. I.)
40 g Patschuliöl 100 g Methyljonon 30 g Ylang-Ylang-öl
150 g Linalylazetat 150 g Citronellol ίο 200 g Phenyläthanol
30 g eines Gemisches aus 2,4-Dimethyl-6-n-butyl-23-dihydro-6H-pyran, 2,4-Dimethyl-6-n-butyl-5,6-dihydro-2H-pyran
und
ι j 2-Methyl-4-methylen-6-n-butyltetrahydropyran
f = 1,4477)
850 g insgesamt
Jasminkomposition
10 g Zimtsäuremethylester 20 g Methylnaphthylketon 30 g Heliotropiji
g Benzylbenzoat 20 g Indol, i%ig in Diallylphthalat
40 g C-14-Aldehyd, 10%ig in Diäthylphthalat g Benzylazetat
g Alpha-Hexylzimtaldehyd 20 g eines Gemisches aus
2,4-Dimethyl-6-n-butyl-2,3-dihydro-6H-pyran, 2,4-Dimethyl-6-n-butyl-5,6-dihydro-2H-pyran
und
2-Methyl-4-methylen-6-n-butyltetrahydropyran (c/fS = 0,8585, η i?= 1,4477)
g insgesamt
Claims (1)
- Patentanspruch:Riechstoffkomposition, enthaltend eine oder mehrere Verbindungen der FormelnCH1 Cy \HC CH,I iH-C C-H/ \ / \ n-QH, O CH3
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL6802619A NL6802619A (de) | 1968-02-23 | 1968-02-23 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE1908756A1 DE1908756A1 (de) | 1969-09-18 |
| DE1908756B2 DE1908756B2 (de) | 1977-10-06 |
| DE1908756C3 true DE1908756C3 (de) | 1978-06-08 |
Family
ID=19802855
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE1908756A Expired DE1908756C3 (de) | 1968-02-23 | 1969-02-18 | Riechstoffkomposition |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US3681263A (de) |
| JP (1) | JPS535383B1 (de) |
| BE (1) | BE728711A (de) |
| CH (1) | CH508717A (de) |
| DE (1) | DE1908756C3 (de) |
| ES (1) | ES363921A1 (de) |
| FR (1) | FR2002521A1 (de) |
| GB (1) | GB1215256A (de) |
| NL (1) | NL6802619A (de) |
| SE (1) | SE357383B (de) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL7608720A (nl) * | 1975-08-07 | 1977-02-09 | Naarden International Nv | Werkwijze voor het bereiden van deodorise- ringspreparaten. |
| ATE5083T1 (de) * | 1979-05-04 | 1983-11-15 | Bush Boake Allen Limited | Riechstoff-komposition. |
| JPS61178977A (ja) * | 1985-01-23 | 1986-08-11 | Kao Corp | ピラン誘導体およびその製造法ならびにそれを含有する香料組成物 |
| JPH01222830A (ja) * | 1988-03-01 | 1989-09-06 | Kubota Ltd | セメント、石膏等より成る型材の自動組立加工装置 |
| US4914083A (en) * | 1989-07-14 | 1990-04-03 | International Flavors & Fragrances Inc. | Oxy-substituted-2-phenyl pyran derivatives and process for preparing same and perfumery uses thereof |
| DE3926170A1 (de) * | 1989-08-08 | 1991-02-14 | Basf Ag | Verfahren zur herstellung von 4-methylentetrahydropyran |
| US4962090A (en) * | 1990-03-22 | 1990-10-09 | International Flavors & Fragrances Inc. | 2,4-disubstituted and 2,2,4-trisubstituted tetrahydropyranyl-4-ethers, process for preparing same and perfumery uses thereof |
| ATE117038T1 (de) * | 1991-05-02 | 1995-01-15 | Hans Seitner | Mauerstein zur aufnahme von versorgungsleitungen. |
| US5378685A (en) * | 1994-03-17 | 1995-01-03 | International Flavors & Fragrances Inc. | Process for preparing mixture of trimethyl and dimethylmethylene propyl polyhydropyrans, products produced thereby perfumery uses of such product |
| EP0834509B1 (de) * | 1996-10-03 | 2005-06-15 | Kao Corporation | Verfahren zur Herstellung von Dihydropyranverbindungen |
| DE19849110C2 (de) * | 1998-10-24 | 2001-12-06 | Bauen Und Ideen Beratungs Plan | Bausatz für ein Mauerwerk |
| GB0216940D0 (en) * | 2002-07-20 | 2002-08-28 | Givaudan Sa | Improvements in or relating to organic compounds |
| US20050004210A1 (en) * | 2003-07-04 | 2005-01-06 | Kao Corporation | Process for producing a pyran compound |
| US7064221B2 (en) * | 2003-09-17 | 2006-06-20 | Kao Corporation | Process for producing pyran |
| JP4545478B2 (ja) * | 2003-09-17 | 2010-09-15 | 花王株式会社 | ピランの製造法 |
| US7875737B2 (en) * | 2006-12-01 | 2011-01-25 | V. Mane Fils | Pyran derivatives, process of preparation and use thereof in perfumery and flavouring |
| EP2125767B1 (de) | 2006-12-01 | 2014-02-26 | V. Mane Fils | Pyran-derivate, verfahren zu ihrer herstellung und ihre verwendung in der parfümerie und aromatisierung |
| EP2112144A1 (de) * | 2008-04-22 | 2009-10-28 | V. Mane Fils | Neuartige Pyranderivate, ihre Zubereitung und Verwendung in der Parfümerie |
| US20090263336A1 (en) * | 2008-04-22 | 2009-10-22 | V. Mane Fils | Novel pyran derivatives and their preparation |
| US9850191B2 (en) * | 2015-03-27 | 2017-12-26 | International Flavors & Fragrances Inc. | Aldehyde compounds and their use in perfume compositions |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2452977A (en) * | 1944-12-28 | 1948-11-02 | Shell Dev | Production of cyclic ethers |
| CH414674A (fr) * | 1961-03-15 | 1966-06-15 | Givaudan & Cie Sa | Procédé pour la préparation de tétrahydro-pyrannes substitués |
| FR1412177A (fr) * | 1963-10-21 | 1965-09-24 | Unilever Nv | Parfums |
-
1968
- 1968-02-23 NL NL6802619A patent/NL6802619A/xx unknown
-
1969
- 1969-02-18 DE DE1908756A patent/DE1908756C3/de not_active Expired
- 1969-02-20 CH CH260269A patent/CH508717A/de not_active IP Right Cessation
- 1969-02-20 SE SE02346/69A patent/SE357383B/xx unknown
- 1969-02-20 BE BE728711D patent/BE728711A/xx not_active IP Right Cessation
- 1969-02-20 US US801005A patent/US3681263A/en not_active Expired - Lifetime
- 1969-02-20 JP JP1224769A patent/JPS535383B1/ja active Pending
- 1969-02-21 GB GB9569/69A patent/GB1215256A/en not_active Expired
- 1969-02-21 ES ES363921A patent/ES363921A1/es not_active Expired
- 1969-02-21 FR FR6904537A patent/FR2002521A1/fr active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| CH508717A (de) | 1971-06-15 |
| JPS535383B1 (de) | 1978-02-27 |
| US3681263A (en) | 1972-08-01 |
| DE1908756A1 (de) | 1969-09-18 |
| FR2002521A1 (de) | 1969-10-17 |
| BE728711A (de) | 1969-08-20 |
| DE1908756B2 (de) | 1977-10-06 |
| SE357383B (de) | 1973-06-25 |
| ES363921A1 (es) | 1971-01-01 |
| GB1215256A (en) | 1970-12-09 |
| NL6802619A (de) | 1969-08-26 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1908756C3 (de) | Riechstoffkomposition | |
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