US3884841A - 2-n-butyl 4,4,6-trimethyl-1,3 dioxane perfume - Google Patents
2-n-butyl 4,4,6-trimethyl-1,3 dioxane perfume Download PDFInfo
- Publication number
- US3884841A US3884841A US456317A US45631774A US3884841A US 3884841 A US3884841 A US 3884841A US 456317 A US456317 A US 456317A US 45631774 A US45631774 A US 45631774A US 3884841 A US3884841 A US 3884841A
- Authority
- US
- United States
- Prior art keywords
- weight
- parts
- trimethyl
- butyl
- perfume
- 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
Links
- 239000002304 perfume Substances 0.000 title abstract description 16
- QUBNQDBPPTZYJL-UHFFFAOYSA-N 2-butyl-4,4,6-trimethyl-1,3-dioxane Chemical compound CCCCC1OC(C)CC(C)(C)O1 QUBNQDBPPTZYJL-UHFFFAOYSA-N 0.000 title description 3
- 239000000203 mixture Substances 0.000 claims abstract description 9
- 238000002360 preparation method Methods 0.000 abstract description 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 239000000796 flavoring agent Substances 0.000 description 6
- 235000019634 flavors Nutrition 0.000 description 6
- 239000003921 oil Substances 0.000 description 4
- 235000019198 oils Nutrition 0.000 description 4
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N pentanal Chemical compound CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 3
- AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 2
- ZCTQGTTXIYCGGC-UHFFFAOYSA-N Benzyl salicylate Chemical compound OC1=CC=CC=C1C(=O)OCC1=CC=CC=C1 ZCTQGTTXIYCGGC-UHFFFAOYSA-N 0.000 description 2
- 241000195940 Bryophyta Species 0.000 description 2
- 244000178870 Lavandula angustifolia Species 0.000 description 2
- 235000010663 Lavandula angustifolia Nutrition 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 2
- 239000006071 cream Substances 0.000 description 2
- -1 cyclic acetal Chemical class 0.000 description 2
- RRAFCDWBNXTKKO-UHFFFAOYSA-N eugenol Chemical compound COC1=CC(CC=C)=CC=C1O RRAFCDWBNXTKKO-UHFFFAOYSA-N 0.000 description 2
- 238000001704 evaporation Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 239000001102 lavandula vera Substances 0.000 description 2
- 235000018219 lavender Nutrition 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 235000011929 mousse Nutrition 0.000 description 2
- 239000000344 soap Substances 0.000 description 2
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 239000001724 (4,8-dimethyl-2-propan-2-ylidene-3,3a,4,5,6,8a-hexahydro-1H-azulen-6-yl) acetate Substances 0.000 description 1
- DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical compound C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- DLHQZZUEERVIGQ-UHFFFAOYSA-N 3,7-dimethyl-3-octanol Chemical compound CCC(C)(O)CCCC(C)C DLHQZZUEERVIGQ-UHFFFAOYSA-N 0.000 description 1
- NFRFQWLJPHVZRK-UHFFFAOYSA-N 4,4,6-trimethyl-1,3-dioxane Chemical compound CC1CC(C)(C)OCO1 NFRFQWLJPHVZRK-UHFFFAOYSA-N 0.000 description 1
- UUGLJVMIFJNVFH-UHFFFAOYSA-N Benzoesaeure-n-hexylester Natural products CCCCCCOC(=O)C1=CC=CC=C1 UUGLJVMIFJNVFH-UHFFFAOYSA-N 0.000 description 1
- NPBVQXIMTZKSBA-UHFFFAOYSA-N Chavibetol Natural products COC1=CC=C(CC=C)C=C1O NPBVQXIMTZKSBA-UHFFFAOYSA-N 0.000 description 1
- 241000723346 Cinnamomum camphora Species 0.000 description 1
- 235000002548 Cistus Nutrition 0.000 description 1
- 241000984090 Cistus Species 0.000 description 1
- 235000005241 Cistus ladanifer Nutrition 0.000 description 1
- 240000008772 Cistus ladanifer Species 0.000 description 1
- 240000007311 Commiphora myrrha Species 0.000 description 1
- 239000005770 Eugenol Substances 0.000 description 1
- 235000018958 Gardenia augusta Nutrition 0.000 description 1
- 239000004869 Labdanum Substances 0.000 description 1
- 244000147568 Laurus nobilis Species 0.000 description 1
- 235000017858 Laurus nobilis Nutrition 0.000 description 1
- 235000006679 Mentha X verticillata Nutrition 0.000 description 1
- 235000002899 Mentha suaveolens Nutrition 0.000 description 1
- 235000001636 Mentha x rotundifolia 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
- 241000219492 Quercus Species 0.000 description 1
- 241001128140 Reseda Species 0.000 description 1
- 241000220317 Rosa Species 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 1
- 235000005212 Terminalia tomentosa Nutrition 0.000 description 1
- 244000284012 Vetiveria zizanioides Species 0.000 description 1
- 235000007769 Vetiveria zizanioides Nutrition 0.000 description 1
- UAVFEMBKDRODDE-UHFFFAOYSA-N Vetiveryl acetate Chemical compound CC1CC(OC(C)=O)C=C(C)C2CC(=C(C)C)CC12 UAVFEMBKDRODDE-UHFFFAOYSA-N 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
- 238000010533 azeotropic distillation Methods 0.000 description 1
- 235000001053 badasse Nutrition 0.000 description 1
- 229960000846 camphor Drugs 0.000 description 1
- 229930008380 camphor Natural products 0.000 description 1
- 239000010627 cedar oil Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000001111 citrus aurantium l. leaf oil Substances 0.000 description 1
- 239000001926 citrus aurantium l. subsp. bergamia wright et arn. oil Substances 0.000 description 1
- 239000012459 cleaning agent Substances 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 229960002217 eugenol Drugs 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000001299 ferula galbaniflua resinoid Substances 0.000 description 1
- 239000000834 fixative Substances 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 239000003517 fume Substances 0.000 description 1
- 239000010648 geranium oil Substances 0.000 description 1
- 235000019717 geranium oil Nutrition 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 244000056931 lavandin Species 0.000 description 1
- 235000009606 lavandin Nutrition 0.000 description 1
- 239000000171 lavandula angustifolia l. flower oil Substances 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 239000012437 perfumed product Substances 0.000 description 1
- 239000001738 pogostemon cablin oil Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000010668 rosemary oil Substances 0.000 description 1
- 229940058206 rosemary oil Drugs 0.000 description 1
- 239000002453 shampoo Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000003760 tallow Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
Images
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
- C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D319/04—1,3-Dioxanes; Hydrogenated 1,3-dioxanes
- C07D319/06—1,3-Dioxanes; Hydrogenated 1,3-dioxanes not condensed with other rings
Definitions
- flavour Green "floral, peppermintlike
- Dependent on the type of composition the dosage 25 2j:n-Butyl-4.4.6-trimethyl-l.3- 160 parts by weight loxane may he between about 5 and about 15% by weight.
- mgthylpmhalme 103 parts by weight a matter of fact in a perfumed product the final concen- 1000 Pans by weight tration will lie much lower.
- 2-n-Butyl-4.4.6-trimethyl-1.3-dioxane may be prepared in the following way:
- the evaporation residue is fractionated in a distillation apparatus with a 40 cm Vigreus-head, at which is obtained: 4 g fore-runnings, boiling point up to 81C/l mm Hg and 170 g 2-n-butyl-4.4 .6-trimethyl-l .3- dioxane boiling point 8l-82C/1 mm Hg; u 1,4295.
- a perfume composition comprising from 5 to 16% of 2-n-butyl-4,4,6-trimethyl-1,3-dioxane in a perfume carrier.
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)
- Cosmetics (AREA)
- Fats And Perfumes (AREA)
- Detergent Compositions (AREA)
- Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL7305487.A NL166187C (nl) | 1973-04-18 | 1973-04-18 | Werkwijze ter bereiding van reukstofcomposities door een 2-gesubstitueerd 4,4,6-trimethyl-1,3-dioxan te mengen met ten minste een andere reukstof en geparfu- meerde voorwerpen. |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3884841A true US3884841A (en) | 1975-05-20 |
Family
ID=19818679
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US456317A Expired - Lifetime US3884841A (en) | 1973-04-18 | 1974-03-29 | 2-n-butyl 4,4,6-trimethyl-1,3 dioxane perfume |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US3884841A (ja) |
| JP (1) | JPS505541A (ja) |
| BE (1) | BE812847A (ja) |
| CH (1) | CH601470A5 (ja) |
| DE (1) | DE2415922C3 (ja) |
| FR (1) | FR2226187B1 (ja) |
| GB (1) | GB1465320A (ja) |
| IT (1) | IT1050471B (ja) |
| NL (1) | NL166187C (ja) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3966647A (en) * | 1974-03-18 | 1976-06-29 | Lever Brothers Company | Perfume compositions containing monoalkyl-para-dioxanes |
| US4124541A (en) * | 1976-06-28 | 1978-11-07 | Henkel Kommanditgesellschaft Auf Aktien | Dioxa bicyclo dodecane and -hexadecane perfume compositions |
| US4146506A (en) * | 1976-10-23 | 1979-03-27 | Henkel Kommanditgesellschaft Auf Aktien (Henkel Kgaa) | Perfume compositions with 4-isopropyl-5,5-dimethyl-1,3-dioxane |
| US4198323A (en) * | 1977-07-29 | 1980-04-15 | Henkel Kommanditgesellschaft Auf Aktien (Henkel Kgaa) | 2,2,5-Trimethyl-5-phenyl-1,3-dioxane and perfume compositions containing it |
| US4211674A (en) * | 1978-04-10 | 1980-07-08 | Polak's Frutal Works B.V. | Cyclic acetals and ketals and their use in perfume compositions |
| US4372880A (en) * | 1980-04-25 | 1983-02-08 | Henkel Kommanditgesellschaft Auf Aktien | Use of substituted 2-(1-methylbutyl)-1,3-dioxanes as perfuming agents |
| EP1316553A1 (de) * | 2001-11-30 | 2003-06-04 | Celanese Chemicals Europe GmbH | Riechstoffe auf Basis cyclischer Acetale |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5939890A (ja) * | 1982-08-26 | 1984-03-05 | Neos Co Ltd | フエニル置換2−(1−アルケニル)−4−イソプロピル−5,5−ジメチル−1,3−ジオキサン誘導体 |
| EP3101112B1 (en) * | 2012-01-18 | 2019-04-03 | The Procter and Gamble Company | Perfume systems |
| CA2908686A1 (en) * | 2013-04-24 | 2014-10-30 | The Procter & Gamble Company | Perfume systems |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB981285A (en) * | 1962-09-04 | 1965-01-20 | Unilever Ltd | Alkylated 1,3-dioxanes and their use as perfumes |
-
1973
- 1973-04-18 NL NL7305487.A patent/NL166187C/xx not_active IP Right Cessation
-
1974
- 1974-03-26 BE BE142464A patent/BE812847A/xx not_active IP Right Cessation
- 1974-03-29 US US456317A patent/US3884841A/en not_active Expired - Lifetime
- 1974-03-29 DE DE2415922A patent/DE2415922C3/de not_active Expired
- 1974-04-05 GB GB1527274A patent/GB1465320A/en not_active Expired
- 1974-04-16 FR FR7413186A patent/FR2226187B1/fr not_active Expired
- 1974-04-16 JP JP49041789A patent/JPS505541A/ja active Pending
- 1974-04-16 IT IT68215/74A patent/IT1050471B/it active
- 1974-04-18 CH CH539274A patent/CH601470A5/xx not_active IP Right Cessation
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB981285A (en) * | 1962-09-04 | 1965-01-20 | Unilever Ltd | Alkylated 1,3-dioxanes and their use as perfumes |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3966647A (en) * | 1974-03-18 | 1976-06-29 | Lever Brothers Company | Perfume compositions containing monoalkyl-para-dioxanes |
| US4124541A (en) * | 1976-06-28 | 1978-11-07 | Henkel Kommanditgesellschaft Auf Aktien | Dioxa bicyclo dodecane and -hexadecane perfume compositions |
| US4146506A (en) * | 1976-10-23 | 1979-03-27 | Henkel Kommanditgesellschaft Auf Aktien (Henkel Kgaa) | Perfume compositions with 4-isopropyl-5,5-dimethyl-1,3-dioxane |
| US4198323A (en) * | 1977-07-29 | 1980-04-15 | Henkel Kommanditgesellschaft Auf Aktien (Henkel Kgaa) | 2,2,5-Trimethyl-5-phenyl-1,3-dioxane and perfume compositions containing it |
| US4211674A (en) * | 1978-04-10 | 1980-07-08 | Polak's Frutal Works B.V. | Cyclic acetals and ketals and their use in perfume compositions |
| US4372880A (en) * | 1980-04-25 | 1983-02-08 | Henkel Kommanditgesellschaft Auf Aktien | Use of substituted 2-(1-methylbutyl)-1,3-dioxanes as perfuming agents |
| EP1316553A1 (de) * | 2001-11-30 | 2003-06-04 | Celanese Chemicals Europe GmbH | Riechstoffe auf Basis cyclischer Acetale |
| EP1481974A1 (de) * | 2001-11-30 | 2004-12-01 | Celanese Chemicals Europe GmbH | Riechstoffe auf Basis cyclischer Acetale |
Also Published As
| Publication number | Publication date |
|---|---|
| IT1050471B (it) | 1981-03-10 |
| DE2415922A1 (de) | 1974-11-07 |
| NL166187C (nl) | 1981-07-15 |
| DE2415922C3 (de) | 1978-06-08 |
| CH601470A5 (ja) | 1978-07-14 |
| BE812847A (nl) | 1974-09-26 |
| NL7305487A (ja) | 1974-10-22 |
| FR2226187A1 (ja) | 1974-11-15 |
| DE2415922B2 (de) | 1977-10-20 |
| GB1465320A (en) | 1977-02-23 |
| JPS505541A (ja) | 1975-01-21 |
| FR2226187B1 (ja) | 1978-01-20 |
| NL166187B (nl) | 1981-02-16 |
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