苦杏仁苷 | 29883-15-6

• 物质功能分类: 生物化工 - 糖类化合物 - 双糖
• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 苦杏仁苷
• 中文别名: D(-)-苦杏仁水合物；苦杏仁甙,苦杏仁苷；扁桃苷；D-扁桃腈6-O-β-D-葡糖基-β-D-葡萄糖苷；苦杏仁素；D-扁桃腈-β-龙胆二糖苷；苦杏仁甙；D-苦杏苷.一水合物
• 英文名称: amygdalin
• 英文别名: (2R)-2-phenyl-2-[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxyacetonitrile
• CAS: 29883-15-6
• 化学式: C₂₀H₂₇NO₁₁
• 分子量: 457.434
• InChiKey: XUCIJNAGGSZNQT-JHSLDZJXSA-N

物化性质

• 熔点：
  223-226 °C
• 比旋光度：
  -38.5 º (c=4, H2O)
• 沸点：
  563.27°C (rough estimate)
• 密度：
  1.4474 (rough estimate)
• 溶解度：
  在热水中的溶解度0.1 g/mL，清澈至微浑浊，无色
• LogP：
  -2.237 (est)
• 旋光度：
  SPECIFIC OPTICAL ROTATION (WATER, C= 1): -42 DEG @ 20 °C/D; SADTLER REF NUMBER: 16450 (IR, PRISM); 5152 (UV)
• 碰撞截面：
  200.6 Ų [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]

计算性质

• 辛醇/水分配系数(LogP)：
  -2.7
• 重原子数：
  32
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  202
• 氢给体数：
  7
• 氢受体数：
  12

ADMET

代谢

苦杏仁苷是一种由葡萄糖、苯甲醛和氰化物组成的化学复合物，后者可以通过β-葡萄糖苷酶或乳化酶的作用释放出来。尽管这些酶在哺乳动物组织中不存在，但人类的肠道微生物群似乎拥有这些或类似的酶，能够促使氰化物的释放，导致人类中毒。因此，与静脉注射相比，通过口服途径摄入的苦杏仁苷可能毒性高达40倍。

AMYGDALIN IS A CHEMICAL COMBINATION OF GLUCOSE, BENZALDEHYDE, & CYANIDE FROM WHICH THE LATTER CAN BE RELEASED BY THE ACTION OF BETA-GLUCOSIDASE OR EMULSIN. ALTHOUGH THESE ENZYMES ARE NOT FOUND IN MAMMALIAN TISSUES, THE HUMAN INTESTINAL MICROFLORA APPEARS TO POSSESS THESE OR SIMILAR ENZYMES CAPABLE OF EFFECTING CYANIDE RELEASE RESULTING IN HUMAN POISONING. FOR THIS REASON AMYGDALIN MAY BE AS MUCH AS 40 TIMES MORE TOXIC BY THE ORAL ROUTE AS COMPARED WITH IV INJECTION.

来源:Hazardous Substances Data Bank (HSDB)

代谢

植物苷类通过酶促或酸性水解产生氰化物，以及糖和芳香醛。常见的例子是苦杏仁中的苦杏仁苷（龙胆二糖+苯甲醛+氢氰酸）。在植物组织中，与苷类共存的一种酶复合物，乳糖酶，催化苷类的水解，首先转化为mandelonitrile或p-羟基mandelonitrile，然后转化为苯甲醛或p-羟基苯甲醛和氢氰酸。这些醛被氧化成相应的芳香酸，并以肽结合物的形式排出体外。

...PLANT GLYCOSIDES ARE CHARACTERIZED BY PRODN OF CYANIDE, TOGETHER WITH A SUGAR & AROMATIC ALDEHYDE, ON ENZYMIC OR ACID HYDROLYSIS. COMMON EXAMPLES ARE AMYGDALIN (GENTIOBIOSE + BENZALDEHYDE + HCN) WHICH IS PRESENT IN BITTER ALMONDS... AN ENZYME COMPLEX, EMULSIN, IS PRESENT TOGETHER WITH GLYCOSIDES IN PLANT TISSUES & CATALYZES THE HYDROLYSIS OF GLYCOSIDES, FIRST TO MANDELONITRILE OR P-HYDROXYMANDELONITRILE, & THEN TO BENZALDEHYDE OR P-HYDROXYBENZALDEHYDE, & HCN. ... THE ALDEHYDES ARE OXIDIZED TO CORRESPONDING AROMATIC ACIDS & EXCRETED AS PEPTIDE CONJUGATES.

来源:Hazardous Substances Data Bank (HSDB)

代谢

各种李属植物含有...苦杏仁苷，它可以通过酶类乳化酶水解...在完整的植物中不会发生此类反应；只有在植物组织受损或开始腐烂时，才会开始释放氢氰酸。

...VARIOUS PRUNUS SPECIES CONTAIN...AMYGDALIN, WHICH IS HYDROLYZED BY ENZYME EMULSIN... IN INTACT PLANT NO SUCH ACTION TAKES PLACE; IT IS NOT UNTIL PLANT TISSUE IS DAMAGED OR STARTS TO DECAY THAT LIBERATION OF HCN BEGINS.

来源:Hazardous Substances Data Bank (HSDB)

代谢

糖苷的分解在瘤胃中通常比单胃动物消化道中更容易或更快发生。此外，小分子可以在瘤胃中被吸收，从而迅速进入循环。来自蔷薇科成员的氰苷糖苷，如苦杏仁苷的分解就是一个例子。

BREAKDOWN /OF GLYCOSIDES/ OFTEN OCCURS MORE READILY OR MORE RAPIDLY IN RUMEN THAN IN DIGESTIVE TRACT OF MONOGASTRIC ANIMALS. ALSO, SMALL MOLECULES CAN BE ABSORBED AT THE RUMEN & THUS ENTER CIRCULATION RAPIDLY. BREAKDOWN OF CYANOGENIC GLYCOSIDES, SUCH AS AMYGDALIN, FROM MEMBERS OF ROSE FAMILY...IS AN EXAMPLE.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 人类毒性摘录

两例苦杏仁苷（杏仁苷）毒性报告，一例为48岁患有淋巴瘤的女性，另一例为46岁患有大细胞未分化肺癌的男性。女性患者在接受每周6毫克静脉注射和每日三次500毫克口服给药后，出现了发热、不适、头痛、严重腹部绞痛、弥漫性斑疹样红斑皮疹、淋巴结病和肝脾肿大。男性患者在接受每日500毫克苦杏仁苷口服给药后，出现了双下肢和上肢进行性神经肌肉无力。两例由口服给药引起的毒性在停药后得到解决。

TWO CASES OF LAETRILE (AMYGDALIN) TOXICITY WERE REPORTED IN A 48-YR-OLD WOMAN WITH LYMPHOMA & A 46-YR-OLD MAN WITH A LARGE CELL ANAPLASTIC CARCINOMA OF THE LUNG. THE WOMAN EXHIBITED FEVER, MALAISE, HEADACHE, SEVERE ABDOMINAL CRAMPS, A DIFFUSE MACULAR ERYTHEMATOUS RASH, LYMPHADENOPATHY & HEPATOSPLENOMEGALY FOLLOWING A WEEKLY 6 MG IV INJECTION & 5OO MG 3 TIMES DAILY ORALLY. THE MAN PRESENTED WITH PROGRESSIVE NEUROMUSCULAR WEAKNESS OF BOTH LOWER & UPPER EXTREMITIES FOLLOWING ORAL ADMIN OF 500 MG OF AMYGDALIN DAILY. BOTH CASES OF TOXICITY RESULTING FROM ORAL ADMIN WAS RESOLVED FOLLOWING DISCONTINUATION OF THE DRUG.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 人类毒性摘录

一位57岁患有乳腺癌的女性因摄入致死剂量的苦杏仁苷（杏仁苷）被送医。入院时，她的氰化物水平为29.0微克/分升。患者在接受对症治疗后有所好转，并被转移到另一家医院，三天后出院。十二天后，患者无生命迹象返回急诊科。尸检显示氰化物水平为218微克/分升，并记录死亡原因为氰化物中毒。

A FATAL LAETRILE (AMYGDALIN) INGESTION BY A 57-YR-OLD FEMALE WITH BREAST CARCINOMA WAS PRESENTED. CYANIDE LEVEL ON ADMISSION TO HOSPITAL WAS 29.0 MCG/DL. THE PT IMPROVED WITH SYMPTOMATIC THERAPY & WAS TRANSFERRED TO ANOTHER HOSPITAL FROM WHICH SHE WAS DISCHARGED 3 DAYS LATER. TWELVE DAYS LATER, THE PT WAS RETURNED TO THE EMERGENCY DEPARTMENT WITH NO SIGN OF LIFE. AN AUTOPSY REVEALED A CYANIDE LEVEL OF 218 MCG/DL & DOCUMENTED THE CAUSE OF DEATH AS CYANIDE POISONING.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 人类毒性摘录

一名48岁的女性在连续9天服用杏仁苷（苦杏仁苷）后，发生了一起严重的氰化物中毒案例，几乎致命。杏仁苷通过静脉注射、肌肉注射、口服和直肠给药，同时配合“排毒饮食”。入院时血液中氰化物的水平为116微克/分升。

A NEAR FATAL CASE OF CYANIDE POISONING IS REPORTED IN A 48-YR-OLD WOMAN AFTER A 9 DAY COURSE OF LAETRILE (AMYGDALIN). LAETRILE WAS ADMIN IV, IM, ORALLY, & RECTALLY ALONG WITH A "DETOXIFICATION DIET". BLOOD LEVELS OF CYANIDE ON ADMISSION WERE 116 MUG/DL.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 人类毒性摘录

两起儿童食用杏核后发生的氰化物中毒事件。第一起事件涉及8名儿童，在摄入大量杏核后2小时表现出典型的氰化物中毒症状和体征；其中7名儿童康复，1名儿童死亡。第二起事件涉及16名儿童，他们食用了用杏核制作的甜食。症状和体征与第一组相同，但在摄入后半小时出现且非常严重。其中三名儿童死亡。

TWO EPISODES OF CYANIDE POISONING OCCURRED IN CHILDREN AFTER INGESTION OF APRICOT KERNELS. THE 1ST EPISODE INVOLVED 8 CHILDREN WHO EXHIBITED TYPICAL SIGNS & SYMPTOMS OF CYANIDE POISONING 2 HR AFTER INGESTION OF LARGE AMOUNTS; 7 CHILDREN RECOVERED & 1 DIED. THE 2ND EPISODE INVOLVED 16 CHILDREN WHO HAD EATEN SWEETS PREPARED FROM KERNELS. SYMPTOMS & SIGNS WERE THE SAME AS THOSE IN THE 1ST GROUP BUT APPEARED 1/2 HR AFTER INGESTION & WERE VERY SEVERE. THREE OF THE CHILDREN DIED.

来源:Hazardous Substances Data Bank (HSDB)

毒理性

• 人类毒性摘录

苦杏仁苷是由葡萄糖、苯甲醛和氰化物组成的化学复合物，后者可以释放出来...苦杏仁苷是苦杏仁素的主要成分，这种据称具有抗癌作用的药物也曾导致人类氰化物中毒。

AMYGDALIN IS A CHEMICAL COMBINATION OF GLUCOSE, BENZALDEHYDE, & CYANIDE FROM WHICH THE LATTER CAN BE RELEASED... AMYGDALIN IS THE MAJOR INGREDIENT OF LAETRILE, & THIS ALLEGED ANTICANCER DRUG HAS ALSO BEEN RESPONSIBLE FOR HUMAN CYANIDE POISONING.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

口服苦杏仁苷给小鼠后，苦杏仁苷释放的氰化物的最大浓度在大约1.5-2小时达到，并且与注射KCN（氰化钾）后观察到的值范围相似。评估了消化道各个区域内容物以及肿瘤组织从苦杏仁苷中释放氰化物的能力。胃和上肠的活性较低，而小肠和粪便则释放了大量氰化物。小鼠之间的差异很大。

THE MAX CYANIDE LEVEL AFTER ORAL ADMIN OF AMYGDALIN TO MICE WAS REACHED AT ABOUT 1 1/2-2 HR & WAS WITHIN THE RANGE OF VALUES SEEN AFTER KCN ADMIN. THE ABILITY OF THE CONTENTS OF VARIOUS REGIONS OF THE GI TRACT & OF TUMOR TISSUE TO RELEASE CYANIDE FROM AMYGDALIN WAS ASSESSED. THE STOMACH & UPPER INTESTINE HAD LITTLE ACTIVITY WHILE THE LOWER INTESTINE & FECES RELEASED LARGE AMOUNTS. THERE WAS A LARGE VARIATION BETWEEN MICE.

来源:Hazardous Substances Data Bank (HSDB)

安全信息

• 危险等级：
  6.1(b)
• 危险品标志：
  Xn
• 安全说明：
  S26,S36/37/39,S45
• 危险类别码：
  R22
• WGK Germany：
  3
• 海关编码：
  29389090
• 危险品运输编号：
  2811
• 危险类别：
  6.1(b)
• RTECS号：
  OO8450000
• 包装等级：
  III
• 危险性防范说明：
  P280,P305+P351+P338
• 危险性描述：
  H302

制备方法与用途

苦杏仁苷简介

苦杏仁中含有一种β-生氰的糖苷，分子中含有氰基(CN)。食用后，该化合物会释放自由的氰基，导致中毒现象；它实际上是苦杏仁中苯丙氨酸代谢的一种产物。

来源

苦杏仁苷（Amygdalin）又名苦杏仁苷，是一种在许多植物中发现的有毒氰苷，尤其以杏、苦杏仁、苹果、桃及梅子等植物种子中最为突出。此外，该物质还存在于其他李属植物如杏和黑樱桃，以及枇杷的叶、果和核里。

配糖物

许多植物根部的细胞含有配糖物，在水解后会产生有毒物质，导致细胞死亡。以桃根中的扁桃苷为例，它是一种氰化糖苷，在水解作用下会产生氢氰酸（HCN）和苯甲醛两种毒素。穿刺短体线虫能够促使这种化学反应发生。

功效与作用

杏仁含有3%的苦杏仁甙。经酶分解后产生氢氰酸，虽然毒性较强但少量使用对呼吸中枢有镇静效果，因此被认为具有一定的镇咳平喘功效，并且具备杀死伤寒杆菌及其他菌类的能力。近年来的研究还发现氢氰酸具有抗癌作用。

化学性质

苦杏仁苷来源于蔷薇科植物东北苦杏仁的干燥成熟种子。

用途

作为一种含葡糖苷的氰化物，它可以作为基质用于鉴别、区分和表征麦芽糖酶、杏仁酪以及β-葡萄糖苷酶等。此外，它还可以用作底物来鉴定、鉴别并表征麦芽糖酶、乳清酶和β-葡萄糖苷酶等多种酶。

类别

有毒物品

毒性分级

高毒

急性毒性

口服 - 大鼠LD50: 522毫克/公斤；口服 - 小鼠LD50: 443毫克/公斤

可燃性危险特性

可燃；受热会产生有毒氮氧化物烟雾

储运特性

库房通风、低温干燥

灭火剂

干粉、泡沫、砂土、二氧化碳

反应信息

• 作为反应物：
  描述：

  苦杏仁苷 在 emulsin 、 水 作用下， 生成 扁桃腈
  参考文献：
  名称：

  Pituitary prolactin-secreting macroadenoma combined with bilateral breast cancer in a 45-year-old male

  摘要：

  We describe an unusual case of bilateral breast cancer synchronous with pituitary macroprolactinoma in a young male. Up to date, only very few of such cases have been described worldwide and to our knowledge this is the first one in which both breast cancer and pituitary macroadenoma have been found together at the time of presentation. A 45-year-old male was diagnosed as having a pituitary macroprolactinoma and bilateral breast cancer on the basis of hypogonadism (testosterone 2.9 pmol/l) with very high levels of prolactin (33,100 U/l), typical neuroradiologic finding of a pituitary macroadenoma, marked bilateral gynecomastia with mammographic pattern highly suspected for cancer and subsequent hystological confirmation. Bilateral mastectomy was performed and medical therapy with bromocriptine 10 mg/day was started. After 2-year follow-up the patient is disease-free. Hormonal, neuroradiological and oncological patterns are all negative or markedly improved. We stress the importance of prolactin for its possible biological effects on breast cancer induction or growth. Moreover in any case of hyperprolactinemia we suggest a mammographic examination and, in the case of breast cancer, at least a baseline hormonal profile. (J. Endocrinol. Invest. 24: 454-459, 2001) (C) 2001, Editrice Kurtis.

  DOI：

  10.1007/bf03351047
• 作为产物：
  描述：

  (R)-(6-O-β-D-glucopyranosyl-β-D-glucopyranosyloxy)(phenyl)acetamide 在 吡啶 、 三氟乙酸酐 作用下， 以 1,4-二氧六环 为溶剂， 反应 2.0h， 以20 mg的产率得到苦杏仁苷
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Cyanogenic Glycosides

  摘要：

  An efficient procedure for the synthesis of cyanogenic glycosides with different carbohydrate units was developed. Amygdalin (3), prunasin (1), sambunigrin (2), and neoamygdalin (21) were prepared according to the elaborated method, and biological tests, including antifungal, antibacterial, and cytotoxic activities, were performed.

  DOI：

  10.1080/07328303.2015.1105249

文献信息

• Expression and Biochemical Characterization of β-Primeverosidase and Application of β-Primeverosylamidine to Affinity Purification
  作者：Hiromichi SAINO、Masaharu MIZUTANI、Jun HIRATAKE、Kanzo SAKATA

  DOI：10.1271/bbb.70447

  日期：2008.2.23

  β-Primeverosidase (PD) is a family 1 glycosidase catalyzing the hydrolysis of β-primeverosides (6-O-β-d-xylopyranosyl-β-d-glucopyranosides) to release a disaccharide primeverose. To investigate how PD recognizes the disaccharide moiety of β-primeverosides, the recombinant PD was expressed by a baculovirus-insect cell system. The recombinant PD was secreted from High Five cells and was properly modified with N-glycosylation and correct cleavage at the N-terminal signal peptide. The recombinant PD exhibited high substrate specificity to β-primeverosides in terms of the glycone moiety, consistently with the substrate specificity of native PD from Camellia sinensis. Next, β-glycosylamidines were synthesized as substrate analog inhibitors. β-Primeverosylamidine strongly inhibited PD activity, but β-glucosylamidine did not. Hence β-primeverosylamidine is an ideal chemical tool for probing disaccharide recognition in the active site of PD. An affinity adsorbent for PD was prepared using β-primeverosylamidine as a ligand. Affinity chromatography gave large amounts of PD with high purity, permitting crystallographic study.

  β-Primeverosidase（PD）是一种家族1糖苷酶，催化β-早春花苷（6-O-β-d-木糖吡喃糖基-β-d-葡萄吡喃糖苷）水解，释放出早春花二糖。为了研究PD如何识别β-早春花苷的二糖部分，我们通过杆状病毒-昆虫细胞系统表达了重组PD。重组PD从High Five细胞中分泌出来，并进行了N-糖基化修饰和N端信号肽的正确切割。重组PD对β-早春花苷的糖苷部分表现出高度的底物特异性，与茶树中天然PD的底物特异性一致。接下来，合成了β-糖苷酰胺作为底物类似物抑制剂。β-早春花苷酰胺强烈抑制PD活性，而β-葡萄糖苷酰胺没有抑制作用。因此，β-早春花苷酰胺是一个理想的化学工具，用于探测PD活性位点中二糖的识别。使用β-早春花苷酰胺作为配体制备了PD的亲和吸附剂。亲和层析获得了高纯度的大量PD，允许进行晶体学研究。
• Mycobacterium tuberculosis β-gentiobiosyl diacylglycerides signal through the pattern recognition receptor Mincle: total synthesis and structure activity relationships
  作者：Mark B. Richardson、Shota Torigoe、Sho Yamasaki、Spencer J. Williams

  DOI：10.1039/c5cc04773k

  日期：——

  Gentiobiosyl diglycerides fromMycobacterium tuberculosisare shown to signal through Mincle; structure–activity relationships reveal analogues with enhanced potency.

  结核分枝杆菌中的甘露二糖基二甘油酸被证明通过Mincle信号传导；结构-活性关系揭示出具有增强效力的类似物。
• [EN] NOVEL EP4 AGONISTS AS THERAPEUTIC COMPOUNDS<br/>[FR] NOUVEAUX AGONISTES DES RÉCEPTEURS EP4 UTILISÉS COMME COMPOSÉS THÉRAPEUTIQUES
  申请人：ALLERGAN INC

  公开号：WO2015188152A1

  公开（公告）日：2015-12-10

  Described herein are compounds that are EP4 agonists and antagonists which are useful for treating a variety of pathological conditions associated with activity of EP4 receptors.

  描述了EP4激动剂和拮抗剂化合物，这些化合物用于治疗与EP4受体活性相关的多种病理状况。
• BITTER TASTE MODIFIERS INCLUDING SUBSTITUTED 1-BENZYL-3-(1-(ISOXAZOL-4-YLMETHYL)-1H-PYRAZOL-4-YL)IMIDAZOLIDINE-2,4-DIONES AND COMPOSITIONS THEREOF
  申请人：SENOMYX, INC.

  公开号：US20160376263A1

  公开（公告）日：2016-12-29

  The present invention includes compounds and compositions known to modify the perception of bitter taste, and combinations of said compositions and compounds with additional compositions, compounds, and products. Exemplary compositions comprise one or more of the following: cooling agents; inactive drug ingredients; active pharmaceutical ingredients; food additives or foodstuffs; flavorants, or flavor enhancers; food or beverage products; bitter compounds; sweeteners; bitterants; sour flavorants; salty flavorants; umami flavorants; plant or animal products; compounds known to be used in pet care products; compounds known to be used in personal care products; compounds known to be used in home products; pharmaceutical preparations; topical preparations; cannabis-derived or cannabis-related products; compounds known to be used in oral care products; beverages; scents, perfumes, or odorants; compounds known to be used in consumer products; silicone compounds; abrasives; surfactants; warming agents; smoking articles; fats, oils, or emulsions; and/or probiotic bacteria or supplements.

  本发明涵盖已知用于改变苦味感知的化合物和组合物，以及所述组合物和化合物与额外的组合物、化合物和产品的组合。示例组合物包括以下一种或多种：冷却剂；无活性药物成分；活性药用成分；食品添加剂或食品；调味剂或调味增强剂；食品或饮料产品；苦味化合物；甜味剂；苦味剂；酸味调味剂；咸味调味剂；鲜味调味剂；植物或动物产品；已知用于宠物护理产品中的化合物；已知用于个人护理产品中的化合物；已知用于家用产品中的化合物；制药制剂；局部制剂；大麻衍生或与大麻相关的产品；已知用于口腔护理产品中的化合物；饮料；香味、香水或除臭剂；已知用于消费品中的化合物；硅化合物；磨料；表面活性剂；发热剂；吸烟物品；脂肪、油脂或乳化剂；和/或益生菌或补充剂。
• USE OF 3-(3-HYDROXY-4-METHOXY-PHENYL)-1-(2,4,6-TRIHYDROXY-PHENYL) PROPAN-1-ONE
  申请人：SYMRISE AG

  公开号：US20190343777A1

  公开（公告）日：2019-11-14

  The present invention concerns the use of 3-(3-Hydroxy-4-methoxy-phenyl)-1-(2,4,6-trihydroxyphenyl)propan-1-one for masking, reducing or suppressing an unpleasant taste impression, preferably bitter, sour and/or astringent taste impression of unpleasant-tasting substances or mixture of substances, preferably bitter-, sour-, and/or astringent-tasting substances or mixtures of substances, and in particular the bitter taste impression of bitter-tasting substances, and/or modulating the taste impressions selected from the group consisting of cooling, umami, fruity and spicy notes of cooling-, umami-, fruity- or spicy-tasting substances or mixture of substances, and simultaneously intensifying the sweet-taste impression of sweet-tasting substances or mixtures of substances or both sweet- and bitter-tasting tasting substances or mixture of substances.

  本发明涉及使用3-(3-羟基-4-甲氧基苯基)-1-(2,4,6-三羟基苯基)丙酮来掩盖、减少或抑制令人不愉快的味觉印象，优选是苦、酸和/或涩的不愉快味觉印象的不愉快味道物质或物质混合物，优选是苦味、酸味和/或涩味物质或物质混合物，特别是苦味物质的苦味印象，和/或调节选自冷却、鲜味、果味和辛辣味的味觉印象的味道物质或物质混合物，同时增强甜味物质或物质混合物或甜味和苦味物质或物质混合物的甜味印象。

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