JP2016537314A - プロピレングリコールを抽出溶媒として使用することによるn−アシルアミノ酸の精製 - Google Patents
プロピレングリコールを抽出溶媒として使用することによるn−アシルアミノ酸の精製 Download PDFInfo
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- JP2016537314A JP2016537314A JP2016519908A JP2016519908A JP2016537314A JP 2016537314 A JP2016537314 A JP 2016537314A JP 2016519908 A JP2016519908 A JP 2016519908A JP 2016519908 A JP2016519908 A JP 2016519908A JP 2016537314 A JP2016537314 A JP 2016537314A
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- 230000035484 reaction time Effects 0.000 description 1
- 235000019203 rebaudioside A Nutrition 0.000 description 1
- 239000013557 residual solvent Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 230000005070 ripening Effects 0.000 description 1
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 1
- 239000010670 sage oil Substances 0.000 description 1
- 208000026451 salivation Diseases 0.000 description 1
- 235000019600 saltiness Nutrition 0.000 description 1
- 235000021491 salty snack Nutrition 0.000 description 1
- 235000014612 sandwich biscuits Nutrition 0.000 description 1
- 150000004671 saturated fatty acids Chemical class 0.000 description 1
- 235000021484 savory snack Nutrition 0.000 description 1
- 230000003248 secreting effect Effects 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 230000001235 sensitizing effect Effects 0.000 description 1
- 235000011803 sesame oil Nutrition 0.000 description 1
- 239000008159 sesame oil Substances 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 235000009561 snack bars Nutrition 0.000 description 1
- 235000012852 snack noodles Nutrition 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 238000007614 solvation Methods 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 235000011497 sour milk drink Nutrition 0.000 description 1
- 235000013322 soy milk Nutrition 0.000 description 1
- 235000011335 soy-based desserts Nutrition 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000019721 spearmint oil Nutrition 0.000 description 1
- 235000013599 spices Nutrition 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 238000005728 strengthening Methods 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 235000011044 succinic acid Nutrition 0.000 description 1
- 235000019408 sucralose Nutrition 0.000 description 1
- BAQAVOSOZGMPRM-QBMZZYIRSA-N sucralose Chemical compound O[C@@H]1[C@@H](O)[C@@H](Cl)[C@@H](CO)O[C@@H]1O[C@@]1(CCl)[C@@H](O)[C@H](O)[C@@H](CCl)O1 BAQAVOSOZGMPRM-QBMZZYIRSA-N 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 239000002600 sunflower oil Substances 0.000 description 1
- 210000000225 synapse Anatomy 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 230000009967 tasteless effect Effects 0.000 description 1
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 1
- 238000002411 thermogravimetry Methods 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 239000010678 thyme oil Substances 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- 235000010487 tragacanth Nutrition 0.000 description 1
- 239000000196 tragacanth Substances 0.000 description 1
- 229940116362 tragacanth Drugs 0.000 description 1
- APXSAEQXOXTDAM-AATRIKPKSA-N trans-10-pentadecenoic acid Chemical compound CCCC\C=C\CCCCCCCCC(O)=O APXSAEQXOXTDAM-AATRIKPKSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- PLSARIKBYIPYPF-UHFFFAOYSA-H trimagnesium dicitrate Chemical compound [Mg+2].[Mg+2].[Mg+2].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O.[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O PLSARIKBYIPYPF-UHFFFAOYSA-H 0.000 description 1
- 150000004043 trisaccharides Chemical class 0.000 description 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
- 235000019607 umami taste sensations Nutrition 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 238000001291 vacuum drying Methods 0.000 description 1
- 239000008371 vanilla flavor Substances 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 239000011345 viscous material Substances 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 235000020234 walnut Nutrition 0.000 description 1
- 235000021119 whey protein Nutrition 0.000 description 1
- 235000015041 whisky Nutrition 0.000 description 1
- 239000009637 wintergreen oil Substances 0.000 description 1
- 235000009764 yeast-based spreads Nutrition 0.000 description 1
- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 1
- FYGDTMLNYKFZSV-BYLHFPJWSA-N β-1,4-galactotrioside Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@H](CO)O[C@@H](O[C@@H]2[C@@H](O[C@@H](O)[C@H](O)[C@H]2O)CO)[C@H](O)[C@H]1O FYGDTMLNYKFZSV-BYLHFPJWSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C231/00—Preparation of carboxylic acid amides
- C07C231/22—Separation; Purification; Stabilisation; Use of additives
- C07C231/24—Separation; Purification
-
- 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
- A23L27/20—Synthetic spices, flavouring agents or condiments
- A23L27/202—Aliphatic compounds
-
- 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
- A23L27/20—Synthetic spices, flavouring agents or condiments
- A23L27/21—Synthetic spices, flavouring agents or condiments containing amino acids
-
- 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
- A23L27/88—Taste or flavour enhancing agents
-
- A—HUMAN NECESSITIES
- A23—FOODS OR FOODSTUFFS; TREATMENT THEREOF, NOT COVERED BY OTHER CLASSES
- A23V—INDEXING SCHEME RELATING TO FOODS, FOODSTUFFS OR NON-ALCOHOLIC BEVERAGES AND LACTIC OR PROPIONIC ACID BACTERIA USED IN FOODSTUFFS OR FOOD PREPARATION
- A23V2002/00—Food compositions, function of food ingredients or processes for food or foodstuffs
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Nutrition Science (AREA)
- Engineering & Computer Science (AREA)
- Food Science & Technology (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Coloring Foods And Improving Nutritive Qualities (AREA)
- Seasonings (AREA)
Abstract
Description
プロピレングリコールは、事実上無味であり、したがってフレーバー用途において使用するために許容し得る。しかしながら、いくらか驚くべきことに、フレーバーベース中に好都合に混入させ得る化合物の適切に濃縮された貯蔵液を作成するために十分な量の式(I)で表される化合物を溶解することが可能であった。
本発明の特定の態様において、少なくとも5%、より特定的には少なくとも10%、尚より特定的には少なくとも15%、尚より特定的には少なくとも25%の式(I)で表される化合物の貯蔵液を提供する。
本発明の尚別の面において、本明細書中に記載した方法に従って生成した本明細書中に記載した貯蔵液を提供する。
R1は、それが結合したカルボニル基と一緒に、カルボン酸、より特に飽和の、または不飽和の脂肪酸の残基であり、R3がHまたはR2およびそれらが結合したN原子と一緒に5員環であるNR2R3は、アミノ酸、特にタンパク新生アミノ酸、オルニチン、ガンマ−アミノ酪酸もしくはベータアラニン、または1−アミノシクロアルキルカルボン酸の残基である、
によって表される。
括弧内の3文字コードは、アミノ酸に関して使用する共通の略号であり、それらを以降使用するものとする。
本発明の特定の態様において、カルボン酸残基は、脂肪酸の残基である。
より特定的には、好ましい脂肪酸残基は、C16〜C18であり、飽和または不飽和であり得る。
特に、式(I)で表される化合物は、D−またはL−アミノ酸の残基を含んでもよい。
R1は、上記に定義され、および
nは、1、2、3または4である、
によって表される。
上記の式において開示したアミノ酸残基は、「ACCA」と略され得る。
化合物は、カルボン酸残基が飽和であるC8−ACCA、C9−ACCA、C10−ACCA、C12−ACCA、C14−ACCA、C16−ACCA、C18−ACCA、C20−ACCAおよびC22−ACCAを含む。
R1は、上記に定義され、および
mは、0または1である、
によって表される。
化合物は、カルボン酸残基が飽和であるC8−GABA、C9−GABA、C10−GABA、C12−GABA、C14−GABA、C16−GABA、C18−GABA、C20−GABAおよびC22−GABAを含む。
化合物は、カルボン酸残基が飽和であるC8−ベータAla、C9−ベータAla、C10−ベータAla、C12−ベータAla、C14−ベータAla、C16−ベータAla、C18−ベータAla、C20−ベータAlaおよびC22−ベータAlaを含む。
好ましい化合物は、C18:2−ベータAlaである。
R1は、上記に定義され、
R3は、水素またはメチルであり、および
R4は、メチル、エチルまたはイソプロピルである、
によって表される。
これらの化合物は、本物感のある果実プロフィールを増強するのに特に有用である。それらはまた、果実フレーバーを有する牛乳、ヨーグルトおよびアイスクリームにおける使用が見出され得る。
化合物は、カルボン酸残基が飽和であるC8−Leu、C9−Leu、C10−Leu、C12−Leu、C14−Leu、C16−Leu、C18−Leu、C20−LeuおよびC22−Leuを含む。
化合物は、カルボン酸残基が飽和であるC8−Ile、C9−Ile、C10−Ile、C12−Ile、C14−Ile、C16−Ile、C18−Ile、C20−IleおよびC22−Ileを含む。
Ile残基を保有する特に好ましい化合物は、N−オレオイル−Ileである。
化合物は、カルボン酸残基が飽和であるC8−Val、C9−Val、C10−Val、C12−Val、C14−Val、C16−Val、C18−Val、C20−ValおよびC22−Valを含む。
R1は、上記に定義される、
によって表される。
これらの化合物は、みずみずしいおいしさおよび典型的な柑橘類の自然度を増強するのに特に有効である。それらは、特に粉末状ソフトドリンクおよび飲料における、ならびにまた乳製品用途、例えば果実フレーバーを有する牛乳、ヨーグルトおよびアイスクリームにおける使用が見出されている。
化合物は、カルボン酸残基が飽和であるC8−Pro、C9−Pro、C10−Pro、C12−Pro、C14−Pro、C16−Pro、C18−Pro、C20−ProおよびC22−Proを含む。
R1は、上記に定義され、
Xは、OHまたはNH2であり、および
Pは、0または1である、
によって表される。
化合物は、カルボン酸残基が飽和であるC8−Glu、C9−Glu、C10−Glu、C12−Glu、C14−Glu、C16−Glu、C18−Glu、C20−GluおよびC22−Gluを含む。
化合物は、カルボン酸残基が飽和であるC8−Asp、C9−Asp、C10−Asp、C12−Asp、C14−Asp、C16−Asp、C18−Asp、C20−AspおよびC22−Aspを含む。
化合物は、カルボン酸残基が飽和であるC8−Gln、C9−Gln、C10−Gln、C12−Gln、C14−Gln、C16−Gln、C18−Gln、C20−GlnおよびC22−Glnを含む。
化合物は、カルボン酸残基が飽和であるC8−Asn、C9−Asn、C10−Asn、C12−Asn、C14−Asn、C16−Asn、C18−Asn、C20−AsnおよびC22−Asnを含む。
R1は上記に定義される、
によって表される。
これらの化合物は、みずみずしいおいしさおよび唾液分泌、ならびに果実の自然度を増強するのに特に有効である。それらはまた、ソフトドリンク用途においてそれらのマスキング特性のために有用である。
化合物は、カルボン酸残基が飽和であるC8−Met、C9−Met、C10−Met、C12−Met、C14−Met、C16−Met、C18−Met、C20−MetおよびC22−Metを含む。
R1は、上記に定義される、
によって表される。
これらの化合物は、低い程度の塩、うまみおよび脂肪、果実のフレーバーを有する飲料および/または乳製品用途において特定の使用が見出される。
化合物は、カルボン酸残基が飽和であるC8−Ser、C9−Ser、C10−Ser、C12−Ser、C14−Ser、C16−Ser、C18−Ser、C20−SerおよびC22−Serを含む。
N−オクタノイル−L−フェニルアラニン、N−エイコサノイル−L−フェニルアラニン、N−パルミトレオイル−L−フェニルアラニン、N−パルミトイル−L−フェニルアラニン、N−リノレノイル−L−フェニルアラニン、N−リノレオイル−L−フェニルアラニン、N−オレオイル−L−フェニルアラニン、N−SDA−L−フェニルアラニン、N−DPA−L−フェニルアラニン、およびN−テトラコサヘキサエノイル−L−フェニルアラニン;
N−パルミトイル−L−アラニン、N−リノレノイル−L−アラニン、N−リノレオイル−L−アラニン;
N−パルミトイル−L−トリプトファン、N−リノレノイル−L−トリプトファン、N−リノレオイル−L−トリプトファン;および
N−リノレオイル−グリシン。
フレーバー共成分は、糖、脂肪、塩(例えば塩化ナトリウム)、MSG、カルシウムイオン、リン酸塩イオン、有機酸、タンパク質、プリンおよびそれらの混合物であり得る。
特定の態様において、脂肪は、食用の製品の合計重量を基準として0.001%〜100%、より特定的には0.001%〜80%、より特定的には0.001%〜30%、尚より特定的には0.001%〜5%の量において存在する。
特定の態様において、MSGは、食用の製品の合計重量を基準として0.001%〜2%の量において存在する。
特定の態様において、有機酸は、食用の製品の合計重量を基準として0.001%〜10%、より特定的には0.001%〜7%の量において存在する。
特定の態様において、プリンは、食用の製品の0.5重量%までの量において存在する。用語「プリン」は、リボヌクレオチド、例えばIMPおよびGMPを含む。
特定の態様において、粉末は、噴霧乾燥プロセスに従って生成する。
同様に、少なくとも摂氏40度のTgを示す、周囲温度および50%相対湿度の条件下で平衡にした担体材料を、高いTgの担体材料と考慮してもよい。Tgを、当該分野において一般に知られているDSC手法を使用して測定することができる。好適な平衡条件を、以下で例において記載する。
本発明の態様において、フレーバー組成物は、式(I)で表される化合物および少なくとも1種のフレーバー共成分を含む。
i)式(I)による化合物;
ii)少なくとも1種のフレーバー共成分;
iii)任意に担体材料;および
iv)任意に少なくとも1種のアジュバント。
用語「フレーバー共成分」は、肯定的な、または心地良い方法で、フレーバー組成物または食用の製品の味に寄与するか、またはそれを付与もしくは修正することができる成分である。
したがって、本発明は、その面の別のものにおいて、粉末フレーバー組成物のフレーバー品質を維持する方法であって、前記粉末フレーバー組成物中に式(I)で表される化合物を混入させるステップを含む、前記方法を提供する。
特定の態様において、食用の製品は、楽しみまたは栄養の目的の1つのために、典型的に口腔を介しての(しかし消費は非経口的手段、例えば吸入を介して生じてもよい)、対象による消費のための製品である。
うまみ味物質を含む食用の製品における興味深い官能的効果、例えばうまみ強化効果を、式(I)で表される化合物(単数または複数)を100〜250ppbのレベルで使用する場合に達成することができる。
脂肪を含む食用の製品における興味深い官能的効果、例えば脂肪強化効果を、式(I)で表される化合物(単数または複数)を500〜1000ppbのレベルで使用する場合に達成することができる。
本発明の別の態様において、式(I)による化合物を含む粉末ソフトドリンク製品または他の乾燥ミックス製品を提供する。
本発明の尚別の面において、粉末フレーバー製品を形成する方法であって、前記組成物中に式(I)による化合物を混入させるステップを含む前記方法を提供する。
式(I)で表される化合物の特定の態様において、形成した粉末フレーバー製品に加えてもよいか、またはそれを、粉末製品を形成する前にフレーバー組成物に加えてもよい。
本出願人は、驚くべきことに、アルコール飲料中に混入されている式(I)による化合物が飲料のアルコールインパクトを増大させる効果を有することを見出した。
本発明の尚別の面において、アルコール飲料における高められたアルコール印象を生じる方法であって、前記飲料中に式(I)による化合物を混入させることによる、前記方法を提供する。
他のクラスの食用の製品は、錠剤、カプセル、粉末、多微粒子(multiparticulate)などの形態で経口的に摂取される製品である。かかる製品は、薬学的投薬形態または薬剤によって栄養価を高めた投薬形態を含んでもよい。
別の好ましいクラスの食用の製品は、焼成食品である。式(I)で表される化合物を、局所的に、または生地中に(in-dough)混入させてもよい。1ppb〜1ppmのレベルで混入されて、式(I)で表される化合物によって、焼成製品は、より乾燥さが少なく、よりジューシーさを付与する。
他の好ましい食用の製品は、食欲をそそる風味のある製品、特に大豆ベースまたは魚ベースであるものである。
別の好ましい食用の製品は、濁った飲料製品である。
したがって、本発明は、その面の別のものにおいて、飲料濁化組成物および式(I)で表される化合物を含む組成物を提供する。
他の好ましい食用の製品は、熟成のプロセスによって生成するものである。
ここで、本発明を例示する役割を果たす一連の非限定的例を後続させる。
製造:
リノレオイルクロリド
1026グラム(3.659モル(100%純度を推測)、1.0当量)のリノール酸(脂肪酸の混合物、リノール酸部分を基準として約60%純度)および8210グラムのTHF(0.13%水)を、反応容器中で一緒に混合した。撹拌し、冷却している(冷却水温度18.6℃)間、948グラム(7.32モル、2.0当量)のオキサリルジクロリド98%(Sigma Aldrich)を、50分において加えた。その後、撹拌を、室温(22℃)で120分間継続した。
プロピレングリコールに溶解した4−((9Z,12Z)−オクタデカ−9,12−ジエンアミド)ブタン酸(C18:2−GABAまたはGABAリノール酸化合物)溶液
反応容器を、7016グラムの水および280.7グラム(7.02モル)の水酸化ナトリウムペレットの混合物で充填した。混合物に、401.5グラム(3.89モル、1.247当量)のガンマアミノ酪酸(GABA)および6244.6グラムのTHFを加えた。撹拌している間に、内容物を10℃に冷却した。1時間の期間にわたって、935.5グラム(3.13モル(100%純度を基準、1.0当量))の前述の方法に従って製造したリノレオイルクロリドを、混合物に加えた。添加中、温度範囲は、10℃〜6.5℃であった。冷却している間に、撹拌を1時間継続し、温度は6.5℃であった。冷却を停止し、撹拌をさらに1時間継続し、温度は8.0℃に上昇した。
例1において生成したGABA−リノール化合物の噴霧乾燥した粉末を、以下の方式において製造した:
400グラムのマルトデキストリン(DE12)を、600グラムの水および26.7グラムのプロピレングリコール溶液(乾燥後に1%のGABA−リノール酸化合物を表す)に加えて、混合物を生成した。混合物を、摂氏20度で等しい容積の水中で激しく撹拌して、供給材料を生成した。供給材料を、Ultra Turrax T25を25,000rpmで約2分間使用して均質化する。均質化した供給材料を、NIRO MOBIL MINOR SPRAY DRYER中で、ロータリーホイールアトマイザー(rotary wheel atomizer)を20,000rpmで使用して噴霧乾燥する。入り口空気温度を190℃で保持し、90℃の範囲内の出口温度をもたらす。
粉末を、デシケーター中で、飽和食塩水上で、50%相対湿度の条件下で2週間平衡にした。その後、平衡にした粉末のTgを、DSC(Perkin Elmer Pyrus Diamond DSC)によって、クローズドカップ法を使用して以下のように測定した:ステンレス鋼カップを、平衡にした粉末で満たし、水が測定の間に蒸発することができないように閉鎖した。DSC測定を、加熱−冷却−加熱測定を使用して試行し、ここで加熱を10℃/分で行い;冷却を40℃/分で行い;および加熱を再び10℃/分で行う。Tg測定を、熱流量を第2の熱サイクルに関する温度に対してプロットしたとき生じた曲線の中間点から計算する。
Claims (13)
- 式(I)による化合物を反応溶媒中に前記化合物を含む反応混合物から単離し、回収する方法であって、反応溶媒の蒸発による除去の前に、反応溶媒より高い沸点を有する化合物のための抽出溶媒を、反応混合物に加え、かつここで化合物の反応溶媒からの分離の後に、式(I)
R1は、それが結合したカルボニル基と一緒に、カルボン酸の残基であり、R3がHまたはR2およびそれらが結合したN原子と一緒に5員環であるNR2R3は、アミノ酸、特にタンパク新生アミノ酸、オルニチン、ガンマ−アミノ酪酸もしくはベータアラニン、または1−アミノシクロアルキルカルボン酸の残基である、
で表される化合物を前記抽出溶媒において貯蔵液の形態で回収することを特徴とする、前記方法。 - 請求項1において定義した式(I)による化合物を反応溶媒中の前記化合物を含む反応混合物から単離し、回収するステップを含む、貯蔵液を生成する方法であって、反応溶媒の蒸発による除去の前に、反応溶媒より高い沸点を有する化合物のための抽出溶媒を、反応混合物に加え、かつここで化合物の反応溶媒からの分離の後に、式(I)で表される化合物を前記抽出溶媒において貯蔵液の形態で回収することを特徴とする、前記方法。
- 抽出溶媒が水混和性アルコールまたはそれらの誘導体からなる群から選択される、請求項1または請求項2に記載の方法。
- 抽出溶媒がエタノール、グリセロール、プロピレングリコール、トリアセチンもしくはミグリオール、またはそれらの混合物である、請求項3に記載の方法。
- 抽出溶媒がプロピレングリコールである、請求項3または請求項4に記載の方法。
- 25重量%までの式(I)で表される化合物を水混和性アルコールまたはそれらの誘導体から選択される溶媒中に含む、貯蔵液。
- 溶媒がエタノール、グリセロール、エチレングリコール、プロピレングリコール、トリアセチンもしくはミグリオール、またはそれらの混合物から選択される、請求項6に記載の貯蔵液。
- 溶媒がプロピレングリコールである、請求項6または請求項7に記載の貯蔵液。
- 式(I)で表される化合物が15重量%までの量において存在する、請求項6〜8のいずれか一項に記載の貯蔵液。
- 式(I)による化合物を含む、噴霧乾燥した粉末。
- 3〜25のデキストロース当量(DE)を有するマルトデキストリンまたはアラビアゴムからなる群から選択される担体材料を含む、請求項10に記載の噴霧乾燥した粉末。
- 式(I)で表される化合物が粉末の合計重量を基準として1.5重量%までの投入量において存在する、請求項10または請求項11に記載の噴霧乾燥した粉末。
- 請求項6〜のいずれか一項に記載の貯蔵液を使用して調製される、請求項10に記載の噴霧乾燥した粉末。
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- 2014-10-01 BR BR112016006877-7A patent/BR112016006877B1/pt active IP Right Grant
- 2014-10-01 EP EP14777628.0A patent/EP3065563A1/en not_active Withdrawn
- 2014-10-01 CN CN201480054461.5A patent/CN105658086B/zh active Active
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Also Published As
Publication number | Publication date |
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BR112016006877A2 (pt) | 2017-08-01 |
EP3065563A1 (en) | 2016-09-14 |
BR112016006877B1 (pt) | 2021-09-21 |
WO2015049275A1 (en) | 2015-04-09 |
CA2924232A1 (en) | 2015-04-09 |
US20160214928A1 (en) | 2016-07-28 |
US10975018B2 (en) | 2021-04-13 |
GB201317424D0 (en) | 2013-11-13 |
CN105658086B (zh) | 2021-04-06 |
CN105658086A (zh) | 2016-06-08 |
JP6599318B2 (ja) | 2019-10-30 |
SG11201601652XA (en) | 2016-04-28 |
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