CN1224343C - 洗涤柑橘油香料的生产方法 - Google Patents
洗涤柑橘油香料的生产方法 Download PDFInfo
- Publication number
- CN1224343C CN1224343C CNB018106315A CN01810631A CN1224343C CN 1224343 C CN1224343 C CN 1224343C CN B018106315 A CNB018106315 A CN B018106315A CN 01810631 A CN01810631 A CN 01810631A CN 1224343 C CN1224343 C CN 1224343C
- Authority
- CN
- China
- Prior art keywords
- oil
- citrus oil
- flavors
- washed citrus
- composition
- 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
- 239000000796 flavoring agent Substances 0.000 title claims abstract description 31
- 235000019634 flavors Nutrition 0.000 title claims abstract description 31
- 238000000034 method Methods 0.000 title claims abstract description 27
- 235000019499 Citrus oil Nutrition 0.000 title claims abstract description 22
- 239000010500 citrus oil Substances 0.000 title claims abstract description 22
- 239000003921 oil Substances 0.000 claims abstract description 39
- 235000019198 oils Nutrition 0.000 claims abstract description 39
- 239000000203 mixture Substances 0.000 claims abstract description 30
- 235000013361 beverage Nutrition 0.000 claims abstract description 7
- 241000207199 Citrus Species 0.000 claims abstract description 4
- 235000020971 citrus fruits Nutrition 0.000 claims abstract description 4
- 241000675108 Citrus tangerina Species 0.000 claims description 23
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 22
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical class CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 claims description 19
- 235000005979 Citrus limon Nutrition 0.000 claims description 10
- 244000131522 Citrus pyriformis Species 0.000 claims description 10
- 244000276331 Citrus maxima Species 0.000 claims description 9
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 9
- 235000001759 Citrus maxima Nutrition 0.000 claims description 8
- 230000002708 enhancing effect Effects 0.000 claims description 4
- 244000089742 Citrus aurantifolia Species 0.000 claims description 3
- 235000008733 Citrus aurantifolia Nutrition 0.000 claims description 3
- 244000175448 Citrus madurensis Species 0.000 claims description 2
- 235000017317 Fortunella Nutrition 0.000 claims description 2
- 244000179970 Monarda didyma Species 0.000 claims description 2
- 235000010672 Monarda didyma Nutrition 0.000 claims description 2
- 235000021028 berry Nutrition 0.000 claims description 2
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 abstract 3
- 239000004615 ingredient Substances 0.000 abstract 1
- WTEVQBCEXWBHNA-JXMROGBWSA-N geranial Chemical compound CC(C)=CCC\C(C)=C\C=O WTEVQBCEXWBHNA-JXMROGBWSA-N 0.000 description 26
- WTEVQBCEXWBHNA-UHFFFAOYSA-N Citral Natural products CC(C)=CCCC(C)=CC=O WTEVQBCEXWBHNA-UHFFFAOYSA-N 0.000 description 14
- 150000001875 compounds Chemical class 0.000 description 14
- 235000013599 spices Nutrition 0.000 description 12
- 239000000047 product Substances 0.000 description 11
- 238000005406 washing Methods 0.000 description 11
- 238000002360 preparation method Methods 0.000 description 10
- KSMVZQYAVGTKIV-UHFFFAOYSA-N decanal Chemical compound CCCCCCCCCC=O KSMVZQYAVGTKIV-UHFFFAOYSA-N 0.000 description 8
- 241000134874 Geraniales Species 0.000 description 7
- WTEVQBCEXWBHNA-YFHOEESVSA-N citral B Natural products CC(C)=CCC\C(C)=C/C=O WTEVQBCEXWBHNA-YFHOEESVSA-N 0.000 description 7
- 238000000605 extraction Methods 0.000 description 7
- XMGQYMWWDOXHJM-UHFFFAOYSA-N limonene Chemical compound CC(=C)C1CCC(C)=CC1 XMGQYMWWDOXHJM-UHFFFAOYSA-N 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- HIGQPQRQIQDZMP-DHZHZOJOSA-N Neryl acetate Natural products CC(C)=CCC\C(C)=C\COC(C)=O HIGQPQRQIQDZMP-DHZHZOJOSA-N 0.000 description 6
- HIGQPQRQIQDZMP-UHFFFAOYSA-N geranil acetate Natural products CC(C)=CCCC(C)=CCOC(C)=O HIGQPQRQIQDZMP-UHFFFAOYSA-N 0.000 description 6
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 5
- 150000001241 acetals Chemical class 0.000 description 5
- 239000000284 extract Substances 0.000 description 5
- 238000011010 flushing procedure Methods 0.000 description 5
- HEVGGTGPGPKZHF-UHFFFAOYSA-N 1-(1,2-dimethyl-3-methylidenecyclopentyl)-4-methylbenzene Chemical compound CC1C(=C)CCC1(C)C1=CC=C(C)C=C1 HEVGGTGPGPKZHF-UHFFFAOYSA-N 0.000 description 4
- QMVPMAAFGQKVCJ-UHFFFAOYSA-N citronellol Chemical compound OCCC(C)CCC=C(C)C QMVPMAAFGQKVCJ-UHFFFAOYSA-N 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- CDOSHBSSFJOMGT-UHFFFAOYSA-N linalool Chemical compound CC(C)=CCCC(C)(O)C=C CDOSHBSSFJOMGT-UHFFFAOYSA-N 0.000 description 4
- NDVASEGYNIMXJL-UHFFFAOYSA-N sabinene Chemical compound C=C1CCC2(C(C)C)C1C2 NDVASEGYNIMXJL-UHFFFAOYSA-N 0.000 description 4
- WTOYNNBCKUYIKC-JMSVASOKSA-N (+)-nootkatone Chemical compound C1C[C@@H](C(C)=C)C[C@@]2(C)[C@H](C)CC(=O)C=C21 WTOYNNBCKUYIKC-JMSVASOKSA-N 0.000 description 3
- 241001441571 Hiodontidae Species 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- WTOYNNBCKUYIKC-UHFFFAOYSA-N dl-nootkatone Natural products C1CC(C(C)=C)CC2(C)C(C)CC(=O)C=C21 WTOYNNBCKUYIKC-UHFFFAOYSA-N 0.000 description 3
- 235000001510 limonene Nutrition 0.000 description 3
- 229940087305 limonene Drugs 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- HIGQPQRQIQDZMP-FLIBITNWSA-N neryl acetate Chemical compound CC(C)=CCC\C(C)=C/COC(C)=O HIGQPQRQIQDZMP-FLIBITNWSA-N 0.000 description 3
- 239000002304 perfume Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- NDVASEGYNIMXJL-NXEZZACHSA-N (+)-sabinene Natural products C=C1CC[C@@]2(C(C)C)[C@@H]1C2 NDVASEGYNIMXJL-NXEZZACHSA-N 0.000 description 2
- XMGQYMWWDOXHJM-JTQLQIEISA-N (+)-α-limonene Chemical compound CC(=C)[C@@H]1CCC(C)=CC1 XMGQYMWWDOXHJM-JTQLQIEISA-N 0.000 description 2
- 239000001490 (3R)-3,7-dimethylocta-1,6-dien-3-ol Substances 0.000 description 2
- QMVPMAAFGQKVCJ-SNVBAGLBSA-N (R)-(+)-citronellol Natural products OCC[C@H](C)CCC=C(C)C QMVPMAAFGQKVCJ-SNVBAGLBSA-N 0.000 description 2
- CDOSHBSSFJOMGT-JTQLQIEISA-N (R)-linalool Natural products CC(C)=CCC[C@@](C)(O)C=C CDOSHBSSFJOMGT-JTQLQIEISA-N 0.000 description 2
- WUOACPNHFRMFPN-SECBINFHSA-N (S)-(-)-alpha-terpineol Chemical compound CC1=CC[C@@H](C(C)(C)O)CC1 WUOACPNHFRMFPN-SECBINFHSA-N 0.000 description 2
- MOYAFQVGZZPNRA-UHFFFAOYSA-N Terpinolene Chemical compound CC(C)=C1CCC(C)=CC1 MOYAFQVGZZPNRA-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- OVKDFILSBMEKLT-UHFFFAOYSA-N alpha-Terpineol Natural products CC(=C)C1(O)CCC(C)=CC1 OVKDFILSBMEKLT-UHFFFAOYSA-N 0.000 description 2
- 229940088601 alpha-terpineol Drugs 0.000 description 2
- KQAZVFVOEIRWHN-UHFFFAOYSA-N alpha-thujene Natural products CC1=CCC2(C(C)C)C1C2 KQAZVFVOEIRWHN-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
- 239000010501 lemon oil Substances 0.000 description 2
- 229930007744 linalool Natural products 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- -1 neral acetic acid esters Chemical class 0.000 description 2
- GYHFUZHODSMOHU-UHFFFAOYSA-N nonanal Chemical compound CCCCCCCCC=O GYHFUZHODSMOHU-UHFFFAOYSA-N 0.000 description 2
- 239000010502 orange oil Substances 0.000 description 2
- 229930006696 sabinene Natural products 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- WTARULDDTDQWMU-RKDXNWHRSA-N (+)-β-pinene Chemical compound C1[C@H]2C(C)(C)[C@@H]1CCC2=C WTARULDDTDQWMU-RKDXNWHRSA-N 0.000 description 1
- FUCYIEXQVQJBKY-ZFWWWQNUSA-N (+)-δ-Cadinene Chemical compound C1CC(C)=C[C@H]2[C@H](C(C)C)CCC(C)=C21 FUCYIEXQVQJBKY-ZFWWWQNUSA-N 0.000 description 1
- WTARULDDTDQWMU-IUCAKERBSA-N (-)-Nopinene Natural products C1[C@@H]2C(C)(C)[C@H]1CCC2=C WTARULDDTDQWMU-IUCAKERBSA-N 0.000 description 1
- XZRVRYFILCSYSP-OAHLLOKOSA-N (-)-beta-bisabolene Chemical compound CC(C)=CCCC(=C)[C@H]1CCC(C)=CC1 XZRVRYFILCSYSP-OAHLLOKOSA-N 0.000 description 1
- 239000001169 1-methyl-4-propan-2-ylcyclohexa-1,4-diene Substances 0.000 description 1
- QPBVYDIIQIYFQO-UHFFFAOYSA-N 3,7-dimethyloct-6-enyl prop-2-enoate Chemical compound CC(C)=CCCC(C)CCOC(=O)C=C QPBVYDIIQIYFQO-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 240000000560 Citrus x paradisi Species 0.000 description 1
- VLXDPFLIRFYIME-GZBLMMOJSA-N Copaene Natural products C1C=C(C)[C@H]2[C@]3(C)CC[C@H](C(C)C)[C@H]2[C@@H]31 VLXDPFLIRFYIME-GZBLMMOJSA-N 0.000 description 1
- PQMOXTJVIYEOQL-UHFFFAOYSA-N Cumarin Natural products CC(C)=CCC1=C(O)C(C(=O)C(C)CC)=C(O)C2=C1OC(=O)C=C2CCC PQMOXTJVIYEOQL-UHFFFAOYSA-N 0.000 description 1
- 235000019500 Grapefruit seed oil Nutrition 0.000 description 1
- 235000019501 Lemon oil Nutrition 0.000 description 1
- FSOGIJPGPZWNGO-UHFFFAOYSA-N Meomammein Natural products CCC(C)C(=O)C1=C(O)C(CC=C(C)C)=C(O)C2=C1OC(=O)C=C2CCC FSOGIJPGPZWNGO-UHFFFAOYSA-N 0.000 description 1
- 235000019502 Orange oil Nutrition 0.000 description 1
- WTARULDDTDQWMU-UHFFFAOYSA-N Pseudopinene Natural products C1C2C(C)(C)C1CCC2=C WTARULDDTDQWMU-UHFFFAOYSA-N 0.000 description 1
- NBZANZVJRKXVBH-GYDPHNCVSA-N alpha-Cryptoxanthin Natural products O[C@H]1CC(C)(C)C(/C=C/C(=C\C=C\C(=C/C=C/C=C(\C=C\C=C(/C=C/[C@H]2C(C)=CCCC2(C)C)\C)/C)\C)/C)=C(C)C1 NBZANZVJRKXVBH-GYDPHNCVSA-N 0.000 description 1
- XCPQUQHBVVXMRQ-UHFFFAOYSA-N alpha-Fenchene Natural products C1CC2C(=C)CC1C2(C)C XCPQUQHBVVXMRQ-UHFFFAOYSA-N 0.000 description 1
- QMAYBMKBYCGXDH-UHFFFAOYSA-N alpha-amorphene Natural products C1CC(C)=CC2C(C(C)C)CC=C(C)C21 QMAYBMKBYCGXDH-UHFFFAOYSA-N 0.000 description 1
- PFXFABJPDNHACA-UHFFFAOYSA-N alpha-copaene Natural products CC(C)C1C2CC(=CCC2C3(C)CC13)C PFXFABJPDNHACA-UHFFFAOYSA-N 0.000 description 1
- XZRVRYFILCSYSP-UHFFFAOYSA-N beta-Bisabolene Natural products CC(C)=CCCC(=C)C1CCC(C)=CC1 XZRVRYFILCSYSP-UHFFFAOYSA-N 0.000 description 1
- FSRZGYRCMPZNJF-UHFFFAOYSA-N beta-Cubebene Natural products C12C(C(C)C)CCC(C)C32C1C(=C)CC3 FSRZGYRCMPZNJF-UHFFFAOYSA-N 0.000 description 1
- FSRZGYRCMPZNJF-KHMAMNHCSA-N beta-cubebene Chemical compound CC(C)[C@@H]([C@H]12)CC[C@@H](C)[C@]32[C@@H]1C(=C)CC3 FSRZGYRCMPZNJF-KHMAMNHCSA-N 0.000 description 1
- 229930006722 beta-pinene Natural products 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000001279 citrus aurantifolia swingle expressed oil Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- VLXDPFLIRFYIME-BTFPBAQTSA-N copaene Chemical compound C1C=C(C)[C@H]2[C@]3(C)CC[C@@H](C(C)C)[C@H]2[C@@H]31 VLXDPFLIRFYIME-BTFPBAQTSA-N 0.000 description 1
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 description 1
- 238000005520 cutting process Methods 0.000 description 1
- 238000010908 decantation Methods 0.000 description 1
- 239000008367 deionised water Substances 0.000 description 1
- 229910021641 deionized water Inorganic materials 0.000 description 1
- YOCDGWMCBBMMGJ-UHFFFAOYSA-N delta-cadinene Natural products C1C=C(C)CC2C(C(C)C)CCC(=C)C21 YOCDGWMCBBMMGJ-UHFFFAOYSA-N 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 239000008369 fruit flavor Substances 0.000 description 1
- LCWMKIHBLJLORW-UHFFFAOYSA-N gamma-carene Natural products C1CC(=C)CC2C(C)(C)C21 LCWMKIHBLJLORW-UHFFFAOYSA-N 0.000 description 1
- 150000002268 gamma-terpinene derivatives Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000007968 orange flavor Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 150000007875 phellandrene derivatives Chemical class 0.000 description 1
- 238000003672 processing method Methods 0.000 description 1
- 239000003507 refrigerant Substances 0.000 description 1
- RXHIKAIVEMAPRU-JRIGQVHBSA-N sequiterpene Natural products C1=C(C)[C@@H](OC(C)=O)[C@H](O)[C@@]2(O)[C@H](C)CC[C@@H](C(C)=C)[C@H]21 RXHIKAIVEMAPRU-JRIGQVHBSA-N 0.000 description 1
- USDOQCCMRDNVAH-UHFFFAOYSA-N sigma-cadinene Natural products C1C=C(C)CC2C(C(C)C)CC=C(C)C21 USDOQCCMRDNVAH-UHFFFAOYSA-N 0.000 description 1
- 230000009897 systematic effect Effects 0.000 description 1
- KMPQYAYAQWNLME-UHFFFAOYSA-N undecanal Chemical compound CCCCCCCCCCC=O KMPQYAYAQWNLME-UHFFFAOYSA-N 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
- 150000008494 α-glucosides Chemical class 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L2/00—Non-alcoholic beverages; Dry compositions or concentrates therefor; Their preparation
- A23L2/52—Adding ingredients
- A23L2/56—Flavouring or bittering agents
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23L—FOODS, FOODSTUFFS, OR NON-ALCOHOLIC BEVERAGES, NOT COVERED BY SUBCLASSES A21D OR A23B-A23J; THEIR PREPARATION OR TREATMENT, e.g. COOKING, MODIFICATION OF NUTRITIVE QUALITIES, PHYSICAL TREATMENT; PRESERVATION OF FOODS OR FOODSTUFFS, IN GENERAL
- A23L27/00—Spices; Flavouring agents or condiments; Artificial sweetening agents; Table salts; Dietetic salt substitutes; Preparation or treatment thereof
- A23L27/10—Natural spices, flavouring agents or condiments; Extracts thereof
- A23L27/12—Natural spices, flavouring agents or condiments; Extracts thereof from fruit, e.g. essential oils
- A23L27/13—Natural spices, flavouring agents or condiments; Extracts thereof from fruit, e.g. essential oils from citrus fruits
-
- 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
- C11B9/02—Recovery or refining of essential oils from raw materials
- C11B9/022—Refining
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Nutrition Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Polymers & Plastics (AREA)
- Food Science & Technology (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Wood Science & Technology (AREA)
- Fats And Perfumes (AREA)
- Seasonings (AREA)
- Non-Alcoholic Beverages (AREA)
- Dairy Products (AREA)
Abstract
可以通过一种方法配制洗涤柑橘油香料，该方法包括采用丙二醇和C1-C4链烷醇的混合物处理柑橘油。获得的洗涤油香料可以用作增香成份，特别是用于透明饮料。
Description
技术领域
本发明涉及香料领域。它更特别地涉及洗涤柑橘油香料的生产方法，该方法包括采用丙二醇和C1-C4链烷醇的混合物处理柑橘油。本发明也涉及采用由本发明方法配制的洗涤柑橘油香料增香的透明饮料。
发明背景
各种柑橘油在香料工业中的重要性已经导致对于加工方法，组成分析，品质和利用的广泛研究。
可以在一些评论中发现涉及商业上很重要的柑橘油的详细组成数据。已经描述了识别为橙子、柚子、橘子、柠檬、和酸橙油组份的各种化合物的广泛列表。
柑橘油的增香特性是在油中识别某些组份性能的函数。此外，d-苎烯，它是存在于柑橘油中的主要组份，作为其它氧化化合物香料的载体是产生柑橘香料特性的主要因素。
因此产生柑橘香料特性的氧化化合物从柑橘油的萃取是香料工业感兴趣的主要领域。在本领域公知的是可以从掺合油萃取在萃取或洗涤得料方面所需的氧化化合物而制备增香剂。
在现有技术中公开的洗涤油香料的配制使用水或丙二醇作为从柑橘油中萃取有用香料化合物的溶剂。例如，美国第3,809,757号专利描述了使用丙二醇和烃溶剂，通过选择萃取从橙油中得到增香萃取物的制备。
萃取物或洗涤物的品质的主要特征为萃取化合物的选择性。因此当从柑橘油配制洗涤物时在香料工业中探索的范围是选择性地获得关键柑橘香料化合物，即，氧化化合物如橙花醛、香叶醛、橙花醛乙酸酯、香叶醛乙酸酯、癸醛、诺卡酮等。其它要求如清澈度或闪点要求对于获得优化洗涤油产品是必须的。
发明描述
现在，结合通常用于氧化化合物萃取的丙二醇，和C1-C4链烷醇，我们已经能够发现洗涤柑橘油香料制备的新颖方法。此方法使得可以获得存在于柑橘油中关键香料化合物的令人惊奇选择性洗涤物，它进一步满足这样产品要求的所有品质和安全性要求。因此本发明涉及一种生产洗涤柑橘油香料的方法，该方法包括采用丙二醇和C1-C4链烷醇的混合物处理柑橘油。在优选的实施方案中，链烷醇选自乙醇和异丙醇。
本发明的方法有利地允许以获得满足在本领域中要求的透明度，闪点和使用量目的的洗涤柑橘油香料。由根据本发明方法获得的洗涤物闪点大于100°F(38℃)(即，它们属于I类液体)，具有在水中的切割透明物(cut clear)和在0.05-0.2％，优选在0.1％使用量下的微量水果香料中的光亮透明轮廓。此外，分别采用和不采用C1-C4链烷醇配制的洗涤柑橘油香料的分析显示出采用一些链烷醇的洗涤产品优于采用丙二醇自身制备的那些。在乙醇的情况下，此结果会在以下对比表中展示。
预想不到的是，并且除C1-C4链烷醇具有低闪点的缺点的事实以外，我们现在能够使用合适量的链烷醇以优化柑橘洗涤油的配制来萃取氧化化合物，同时满足闪点限制。
用于萃取混合物的链烷醇与丙二醇的比例可在一定的数值范围内变化。典型地，它可占组合物总重量的3-10％和优选占5-7％，丙二醇占组合物总重量的75～90％，柑橘油占组合物总重量的5～15％，该组合物包括柑橘油，丙二醇和链烷醇。
如上所述，在C1-C4链烷醇中，优选是乙醇和异丙醇。
本发明方法的起始产品可以是任何市售柑橘油，例如，为冷榨油，或掺合油的形式。可用于本发明方法的柑橘油的非限制性例子包括柠檬、浆果、橙子、柚子、橘子、酸柠檬、金橘、柑桔、香柠檬或其它精油或其混合物。
萃取体系的选择性可以由采用一些乙醇制造的柑橘洗涤物，和采用75％丙二醇∶25％香料油制备的，即无乙醇的洗涤油香料之间的比较展示。
下表比较采用与乙醇结合的丙二醇获得的洗涤物，和采用丙二醇自身获得的那些。
表1显示柠檬洗涤物的结果而表2显示柚子洗涤物结果。
表1
| 化合物 | 百分比 | ||
| 柠檬油 * | 柠檬洗涤物-83％PG-6％EtOH-11％油 | 柠檬洗涤物-75％PG-25％油 | |
| 水芹烯 | 0.75 | 0.39 | 0.36 |
| α蒎烯 | 3.32 | 2.10 | 1.52 |
| 莰烯 | 0.17 | ||
| 桧烯 | 2.30 | 1.80 | |
| β蒎烯 | 19.68 | 16.10 | 10.43 |
| 月桂烯 | 2.45 | 1.56 | 1.61 |
| 苎烯 | 52.70 | 56.41 | 57.26 |
| 罗勒烯 | 0.48 | 0.37 | 0.42 |
| γ-萜品烯 | 10.67 | 8.43 | 7.86 |
| α-萜品油烯 | 0.67 | 0.56 | 0.53 |
| 壬醛 | 0.27 | 0.29 | 0.15 |
| 里哪醇 | 0.11 | 0.23 | 1.84 |
| 香茅醇 | 0.11 | ||
| α-萜品醇 | 0.22 | 0.35 | 3.31 |
| 癸醛 | 0.12 | ||
| 橙花醛 | 1.53 | 0.61 | 0.68 |
| 香叶醛 | 2.49 | 0.59 | 0.30 |
| 十一醛 | ＜0.05 | ||
| 醛酸香茅酯 | 0.06 | ||
| 橙花醇乙酸酯 | 1.25 | 1.14 | 0.66 |
| 醋酸香叶酯 | 0.75 | 0.60 | 0.30 |
| 石竹烯 | 0.46 | ||
| 橙花醛/pg乙缩醛 | 1.48 | 2.31 | |
| A倍半萜 | 0.70 | ||
| 橙花醛/pg乙缩醛 | 0.95 | 1.50 | |
| 香叶醛/pg乙缩醛 | 3.29 | 4.23 | |
| 香叶醛/pg乙缩醛 | 2.26 | 2.92 | |
| β-红没药烯 | 1.00 | ||
*来源：弗门尼舍柑橘中心，佛罗里达，美国
表2
| 化合物 | 百分比 | ||
| 柚子油 * | 柚子洗涤物-83％PG-6％EtOH-11％油 | 柚子洗涤物-75％PG-25％油 | |
| α蒎烯 | 0.52 | 2.08 | |
| 桧烯 | 0.31 | ||
| 月桂烯 | 2.51 | ||
| 苎烯 | 75.04 | 80.55 | |
| 罗勒烯 | 0.51 | 0.71 | |
| 壬醛 | 0.35 | 0.39 | |
| 里哪醇 | 0.68 | 0.85 | |
| 氧化苎烯 | 0.31 | ||
| 香茅醇 | 0.51 | ||
| α-萜品醇 | 2.13 | 2.51 | 39.74 |
| 癸醛 | 2.62 | 3.14 | |
| 乙酸辛酯 | 0.58 | 0.47 | |
| 橙花醛 | 0.40 | ||
| 香叶醛 | 0.47 | ||
| 橙花醇乙酸酯 | 0.08 | ||
| 乙酸香叶酯 | 0.37 | ||
| α-可巴烯 | 0.96 | ||
| β-荜澄茄油烯 | 0.89 | ||
| 石竹烯 | 2.60 | 0.84 | |
| α-甙草烯 | 0.43 | ||
| Pg乙缩醛 | 0.90 | ||
| δ-杜松烯 | 0.88 | ||
| 诺卡酮 | 2.86 | 3.40 | |
| α-香豆素 | 0.69 | 2.10 | 60.26 |
| α-苯并吡喃酮 | 3.31 | 2.05 | |
*来源：弗门尼舍柑橘中心，佛罗里达，美国
可以容易地从上表中报导的结果得出结论，在从柑橘油萃取关键香料化合物(即氧化化合物如橙花醛、香叶醛、乙酸香叶酯、橙花醇乙酸酯、癸醛、诺卡酮等)中一些乙醇的使用是有利的。
本发明也涉及一种用于赋予、促进、增强或改进增香组合物或增香产品增香性能的方法，该方法包括向该组合物或产品中加入由本发明方法生产的洗涤柑橘油香料。
本发明的另一个目的是增香组合物或增香产品如透明饮料，其包括洗涤柑橘油香料作为活性增香成份，后者包括的比例为组合物或产品总重量的0.05-0.2％。
在以下实施例中以更详细的方式说明本发明，其中温度指示为摄氏度和缩写具有本领域的通常意义。
发明实施方案
实施例1
生产洗涤柑橘油香料的通用加工程序
●开启冷冻到-8°
●向大约10-12°温度下的混合物罐中加入所需量的香料油
●向大约10-12°温度下的混合物罐中加入所需量的链烷醇
●剧烈搅拌混合油和链烷醇20min。(调节搅拌以避免气泡)
●切断搅拌
●向21°温度下的混合物罐中加入所需量的丙二醇
●罐的温度须在19-23°
●开启搅拌剧烈混合20min，不向溶液中加入空气
●调低搅拌到大约10-15rpm
●开启混合物罐冷却夹套
●采用低搅拌(即10-15rpm)冷却大约一小时。当温度达到0-5°时切断搅拌
●继续冷却罐内容物另外3小时到大约-2°到0°，不采用搅拌
●在聚结器产物罐夹套上开启冷却
●在大约2.6-3.0kg/min的速率下将结合罐内容物通过帕尔(Pall)五微米和一微米过滤器(可选的：可以通过威斯特法利亚(Westfalia)离心机离心产物。优选是液-液离心)。在-2°到0°下滗析聚结器产物罐中的内容物2小时
●开启冷冻剂到最终产物罐夹套
●产物在饮料应用中是透明的，在3°下使用量为0.05-0.2％
香料生产
一旦确定产物配制和加工程序，采用丙二醇和乙醇的混合物，生产如下香料：
-天然酸柠檬香料*
-天然粉红柚子香料*
-天然柚子香料*
-天然橙子香料*
-天然柠檬香料*
*油来源：弗门尼舍柑橘中心，佛罗里达，美国
表3显示柑橘洗涤物的配方
表3
| 酸柠檬 | 粉红柚子 | 柚子 | 橙子 | 柠檬 | |
| 丙二醇[％] | 83.3 | 83.3 | 83.3 | 83.3 | 83.3 |
| 去离子水[％] | 0 | 0 | 0 | 0 | 0 |
| 乙醇[％] | 6.3 | 6.3 | 6.3 | 6.3 | 6.3 |
| 油量[％] | 10.4 | 10.4 | 10.4 | 10.4 | 10.4 |
| 闪点[°F] | 100 | 111 | 102 | 102 | 102 |
随后根据盲测试，由增香领域专家小组评价这样获得的洗涤油香料和与按照上述方法，但仅使用75％丙二醇和25％香料油通过萃取获得的相应洗涤物比较。小组显示出对表3中引用洗涤物的系统性的偏爱，判断它们的感官性能优于不采用乙醇获得的洗涤油香料的那些。
此结果证实了分别在表1和2中报导的柠檬和柚子洗涤物的GC/MSD分析。
Claims (12)
1.一种生产洗涤柑橘油香料的方法，该方法包括采用丙二醇和C1-C4链烷醇的混合物洗涤柑橘油。
2.根据权利要求1所述的方法，其中所述链烷醇选自乙醇和异丙醇。
3.根据权利要求1所述的方法，其中所述洗涤柑橘油香料具有大于100°F的闪点。
4.根据权利要求1所述的方法，其中所述柑橘油得自柠檬、浆果、橙子、柚子、橘子、酸柠檬、金橘、柑桔、香柠檬或其混合物。
5.根据权利要求1所述的方法，其中采用75-90％丙二醇和3-10％链烷醇处理5-15％柑橘油，上述含量百分比以丙二醇、链烷醇和柑橘油的组合物的总重量为基础。
6.一种根据权利要求1所述的方法获得的洗涤柑橘油香料。
7.一种增香组合物，包括权利要求6所述的洗涤柑橘油香料作为活性增香成份。
8.根据权利要求7所述的增香组合物，其中所述洗涤柑橘油香料的比例为所述组合物总重量的0.05-0.2％。
9.一种增香过的产品，包括权利要求6所述的洗涤柑橘油香料作为活性增香成份。
10.根据权利要求9所述的增香过的产品，其中所述洗涤柑橘油香料的比例为所述产品总重量的0.05-0.2％。
11.一种透明饮料，包括权利要求6所述的洗涤柑橘油香料作为增香剂。
12.根据权利要求11所述的透明饮料，该饮料被0.05-0.2％的如权利要求6所述的洗涤柑橘油香料增香。
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US09/586,754 US6458408B1 (en) | 2000-06-05 | 2000-06-05 | Process for producing washed citrus oil flavors |
| US09/586,754 | 2000-06-05 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1438841A CN1438841A (zh) | 2003-08-27 |
| CN1224343C true CN1224343C (zh) | 2005-10-26 |
Family
ID=24346993
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB018106315A Expired - Lifetime CN1224343C (zh) | 2000-06-05 | 2001-05-28 | 洗涤柑橘油香料的生产方法 |
Country Status (12)
| Country | Link |
|---|---|
| US (2) | US6458408B1 (zh) |
| EP (1) | EP1292199B2 (zh) |
| JP (1) | JP5044082B2 (zh) |
| CN (1) | CN1224343C (zh) |
| AR (1) | AR028121A1 (zh) |
| AT (1) | ATE345698T1 (zh) |
| BR (1) | BR0111332B1 (zh) |
| DE (2) | DE60124707T4 (zh) |
| ES (1) | ES2274885T5 (zh) |
| MX (1) | MXPA02012009A (zh) |
| SA (1) | SA01220199B1 (zh) |
| WO (1) | WO2001093703A2 (zh) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9155769B2 (en) | 2006-07-07 | 2015-10-13 | The Procter & Gamble Co | Flavor oils with reduced dimethyl sulfoxide content and use in oral compositions |
| AU2013201477B2 (en) * | 2006-07-07 | 2015-06-18 | The Procter & Gamble Company | Flavor oils with reduced sulfur content and use in oral care compositions |
| CN101578052B (zh) * | 2006-09-25 | 2014-01-01 | 鲍勃·康斯托克 | 用于溶解香料油的工艺 |
| JP5546961B2 (ja) * | 2010-06-15 | 2014-07-09 | 長谷川香料株式会社 | 水溶性抽出液の製造方法 |
| JP5161943B2 (ja) * | 2010-09-17 | 2013-03-13 | 麒麟麦酒株式会社 | イソプロパノールを含んでなるリモネン含有飲料 |
| US8939388B1 (en) | 2010-09-27 | 2015-01-27 | ZoomEssence, Inc. | Methods and apparatus for low heat spray drying |
| US9332776B1 (en) | 2010-09-27 | 2016-05-10 | ZoomEssence, Inc. | Methods and apparatus for low heat spray drying |
| IN2014CN00736A (zh) * | 2011-08-29 | 2015-04-03 | Firmenich & Cie | |
| CA2866246C (en) | 2012-03-09 | 2020-01-28 | Kraft Foods Group Brands Llc | Food and beverage products containing 1,3-propanediol and methods of suppressing bitterness and enhancing sweetness in food and beverage products using 1,3-propanediol |
| EP2822401B1 (en) | 2012-03-09 | 2018-10-31 | Kraft Foods Group Brands LLC | Oxidized flavor note suppression in comestibles |
| US10774288B2 (en) * | 2013-09-18 | 2020-09-15 | The Werc Shop, LLC | Terpene-based compositions, processes, methodologies for creation and products thereby |
| ES2776385T3 (es) | 2014-11-13 | 2020-07-30 | Cargill Inc | Bebida transparente que comprende una emulsión Ac/Ag |
| US10172349B2 (en) * | 2016-09-08 | 2019-01-08 | Bedoukian Research, Inc. | Formulations for control and repellency of biting arthropods |
| US9861945B1 (en) | 2017-08-04 | 2018-01-09 | ZoomEssence, Inc. | Ultrahigh efficiency spray drying apparatus and process |
| WO2019028446A1 (en) | 2017-08-04 | 2019-02-07 | ZoomEssence, Inc. | APPARATUS AND METHOD FOR HIGH-PERFORMANCE SPRAY DRYING |
| US10486173B2 (en) | 2017-08-04 | 2019-11-26 | ZoomEssence, Inc. | Ultrahigh efficiency spray drying apparatus and process |
| US10155234B1 (en) | 2017-08-04 | 2018-12-18 | ZoomEssence, Inc. | Ultrahigh efficiency spray drying apparatus and process |
| US9993787B1 (en) | 2017-08-04 | 2018-06-12 | ZoomEssence, Inc. | Ultrahigh efficiency spray drying apparatus and process |
| JP7341636B2 (ja) * | 2017-12-05 | 2023-09-11 | アサヒビール株式会社 | 果汁含有飲料 |
| US10569244B2 (en) | 2018-04-28 | 2020-02-25 | ZoomEssence, Inc. | Low temperature spray drying of carrier-free compositions |
| CN108618103B (zh) * | 2018-05-10 | 2021-08-17 | 上海应用技术大学 | 一种柚子香精及其制备方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3809757A (en) * | 1971-09-17 | 1974-05-07 | Nestle Sa | Flavouring agent |
| US4497838A (en) * | 1982-02-17 | 1985-02-05 | Tropicana Products, Inc. | Process for the production of useful products from orange peel |
| JPS5924795A (ja) * | 1982-08-02 | 1984-02-08 | 長谷川香料株式会社 | 脱テルペン化精油の製法 |
-
2000
- 2000-06-05 US US09/586,754 patent/US6458408B1/en not_active Expired - Lifetime
-
2001
- 2001-05-28 DE DE60124707T patent/DE60124707T4/de not_active Expired - Lifetime
- 2001-05-28 MX MXPA02012009A patent/MXPA02012009A/es active IP Right Grant
- 2001-05-28 DE DE60124707A patent/DE60124707D1/de not_active Expired - Lifetime
- 2001-05-28 AT AT01932016T patent/ATE345698T1/de not_active IP Right Cessation
- 2001-05-28 ES ES01932016T patent/ES2274885T5/es not_active Expired - Lifetime
- 2001-05-28 JP JP2002501279A patent/JP5044082B2/ja not_active Expired - Lifetime
- 2001-05-28 BR BRPI0111332-1A patent/BR0111332B1/pt active IP Right Grant
- 2001-05-28 CN CNB018106315A patent/CN1224343C/zh not_active Expired - Lifetime
- 2001-05-28 EP EP01932016A patent/EP1292199B2/en not_active Expired - Lifetime
- 2001-05-28 WO PCT/IB2001/000939 patent/WO2001093703A2/en active IP Right Grant
- 2001-05-29 AR ARP010102560A patent/AR028121A1/es active IP Right Grant
- 2001-07-04 SA SA01220199A patent/SA01220199B1/ar unknown
-
2002
- 2002-08-20 US US10/225,114 patent/US6709691B2/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| WO2001093703A3 (en) | 2002-05-16 |
| ES2274885T3 (es) | 2007-06-01 |
| BR0111332A (pt) | 2003-06-03 |
| ES2274885T5 (es) | 2012-03-15 |
| DE60124707T3 (de) | 2012-05-16 |
| DE60124707T4 (de) | 2013-02-14 |
| US6709691B2 (en) | 2004-03-23 |
| JP2003535207A (ja) | 2003-11-25 |
| DE60124707D1 (de) | 2007-01-04 |
| US6458408B1 (en) | 2002-10-01 |
| MXPA02012009A (es) | 2003-04-22 |
| US20030021883A1 (en) | 2003-01-30 |
| JP5044082B2 (ja) | 2012-10-10 |
| AR028121A1 (es) | 2003-04-23 |
| DE60124707T2 (de) | 2007-09-13 |
| EP1292199B2 (en) | 2011-12-14 |
| CN1438841A (zh) | 2003-08-27 |
| ATE345698T1 (de) | 2006-12-15 |
| WO2001093703A2 (en) | 2001-12-13 |
| BR0111332B1 (pt) | 2013-05-14 |
| EP1292199A2 (en) | 2003-03-19 |
| SA01220199B1 (ar) | 2006-09-09 |
| EP1292199B1 (en) | 2006-11-22 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN1224343C (zh) | 洗涤柑橘油香料的生产方法 | |
| Yang et al. | Chemical profiles and aroma contribution of terpene compounds in Meili (Vitis vinifera L.) grape and wine | |
| He et al. | Flavor and chiral stability of lemon-flavored hard tea during storage | |
| Strauss et al. | Novel monoterpene diols and diol glycosides in Vitis vinifera grapes | |
| Fenoll et al. | Changes in the aromatic composition of the Vitis vinifera grape Muscat Hamburg during ripening | |
| JP5352194B2 (ja) | 精製エッセンシャルオイルの製造方法 | |
| Tufariello et al. | Volatile components of Negroamaro red wines produced in Apulian Salento area | |
| JP6334894B2 (ja) | 柑橘類果実の浸漬酒 | |
| Oliveira et al. | Volatile and glycosidically bound composition of Loureiro and Alvarinho wines | |
| JP4563272B2 (ja) | 風味強化果汁 | |
| CN1274355A (zh) | 作为调味剂释放化合物的二烷氧羰基二氧戊环化合物 | |
| Zhong et al. | Free and bound volatile compounds in juice and peel of Eureka lemon | |
| AU2015368565B2 (en) | Citrus-derived liquid composition | |
| Rocha et al. | Effect of enzymatic aroma release on the volatile compounds of white wines presenting different aroma potentials | |
| CN1236054C (zh) | 一株降解石油的细菌及其应用 | |
| Njoroge et al. | Essential oils of Kenyan Citrus fruits: volatile components of two varieties of mandarins (Citrus reticulata) and a tangelo (C. paradisi× C. tangerina) | |
| JP2019097428A (ja) | リモネンを含有する柑橘系アルコール飲料 | |
| WO2003061407A1 (en) | Method of making flavedo powder for enhancement of orange juice and products thereof | |
| AU2012212497A1 (en) | Removing compounds from wine | |
| Genisheva et al. | Monoterpenic characterization of white cultivars from Vinhos Verdes appellation of origin (North Portugal) | |
| JP7329357B2 (ja) | 柑橘果実様飲料 | |
| JP7044544B2 (ja) | 芋焼酎、芋焼酎含有炭酸飲料、芋焼酎の製造方法、及び、芋焼酎の香味向上方法 | |
| JP5889593B2 (ja) | アルコール飲料の風味改善剤 | |
| KR102696727B1 (ko) | 사과를 주요성분으로 하는 리큐르 및 이의 제조방법 | |
| Miličević et al. | The effects of the fermentation with immobilized yeast and different cherry varieties on the quality of cherry brandy |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C06 | Publication | ||
| PB01 | Publication | ||
| C10 | Entry into substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| C14 | Grant of patent or utility model | ||
| GR01 | Patent grant | ||
| TR01 | Transfer of patent right |
Effective date of registration: 20200610 Address after: geneva Co-patentee after: FIRMENICH PERFUME (CHINA) Co.,Ltd. Patentee after: FIRMENICH S.A. Address before: geneva Patentee before: FIRMENICH S.A. |
|
| TR01 | Transfer of patent right | ||
| CX01 | Expiry of patent term |
Granted publication date: 20051026 |
|
| CX01 | Expiry of patent term |