CN112638170A - 有机化合物 - Google Patents
有机化合物 Download PDFInfo
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- CN112638170A CN112638170A CN201980035959.XA CN201980035959A CN112638170A CN 112638170 A CN112638170 A CN 112638170A CN 201980035959 A CN201980035959 A CN 201980035959A CN 112638170 A CN112638170 A CN 112638170A
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Abstract
公开了一种抑制消费品中所包含的非动物衍生的蛋白质的异味的方法。更具体地,本公开涉及环己酸乙酯和包含环己酸乙酯的香味组合物在包含非动物衍生的蛋白质的消费品中的用途。
Description
本公开涉及抑制消费品中所包含的非动物衍生的蛋白质的异味的方法。更具体地,本公开涉及环己酸乙酯和包含环己酸乙酯的香味组合物在包含非动物衍生的蛋白质的消费品中的用途。
由于膳食中蛋白质的益处,所以在食品中使用非动物蛋白质来代替动物原料例如蛋或牛奶和肉类变得越来越重要。虽然消费者期望他们的食品和饮料产品具有多功能效益,但消费者仍然高度期望这些产品在健康益处方面递送良好的味觉和功效。因为每类蛋白质都有其固有的味道,所以将蛋白质配制入食品和饮料产品中可能产生被认为不具吸引力的特征性味道。例如,由植物蛋白例如豆科植物(例如大豆或豌豆)制成的产品显示出被描述为草味、豆腥味、青香味、土壤味、坚果味和/或苦味的风味特征。通常与大豆蛋白和豌豆蛋白相关举出的特定异味为豆腥味、大豆味和苦味属性。与马铃薯蛋白相关举出的异味通常为鱼腥味、青香味、土壤味-发霉味和苦味属性。
因此,仍然需要表现出改善的香味以及减少的异味的非动物蛋白质和包含所述非动物蛋白质的产品。
令人惊奇地发现,向包含非动物蛋白质的产品中添加环己酸乙酯能够提供具有改善的香味特性的消费产品,这归因于抑制或至少减少了异味。
因此,在第一个方面,提供了包含非动物衍生的蛋白质和环己酸乙酯的消费品。
“非动物衍生的蛋白质”是指由原料制成的蛋白质制品,所述原料包括、但不限于谷物(大米,小米,玉米,大麦,小麦,燕麦,高粱,黑麦,埃塞俄比亚画眉草,小黑麦,苋菜,荞麦,藜麦);豆科作物或豆类植物(豆类(例如大豆,绿豆,蚕豆,利马豆,红花菜豆,菜豆(kidney beans),海军豆(navy beans),斑豆,红豆(azuki beans)等);豌豆(例如青豆,黄豆,鹰嘴豆(chickpeas),木豆(pigeon peas),豇豆和黑眼豆(black-eyed peas)等),芝麻,埃及豆(garbanzo),马铃薯,小扁豆和羽扇豆);种子和油料种子(黑芥,印度芥,油菜籽,低芥酸菜子(canola),红花,向日葵子,亚麻子,火麻仁,南瓜,芡欧鼠尾草 (chia),芝麻);坚果(杏仁,胡桃,巴西坚果(Brazil),澳大利亚坚果 (Macadamia),腰果,栗子,榛子,松子(pine),美洲山核桃,花生,阿月浑子果实(pistachio)和银杏);藻类(海草(kelp),裙带菜,螺旋藻,小球藻);菌蛋白或真菌蛋白质。在一个具体的实施方案中,非动物衍生的蛋白质选自大豆蛋白、豌豆蛋白、谷物蛋白(例如小麦、燕麦、大米蛋白)、藻蛋白和蚕豆(faba)蛋白及其混合物。在另一个具体的实施方案中,非动物衍生的蛋白质选自大豆蛋白、豌豆蛋白(例如青豆)、谷物蛋白(例如小麦、燕麦)及其混合物。
已知环己酸乙酯、有时称作环己基甲酸乙酯(CAS 3289-28-9; FEMA No 3544)出现在天然油中,例如来源于橄榄油(参见,例如 Reiners等人,J.Agric.Food Chem.1998,46,2754-2763)和朗姆酒 (rum)(参见Franitza等人,J.Agric.Food Chem.2016,64,637-645)。该化合物具有约1ppt的显著低的气味阈值(Gary R.Takeoka等 人,Lebensm.-Wiss.u.-Technol.,24,569-570(1991)。
令人惊讶地发现,在其气味检测阈值附近使用环己酸乙酯、即约 0.5ppt(ng/L)至约20ppt(ng/L)(包括0.6、0.7、0.8、0.9、1、1.5、2、 2.5、5、7.5、8、9、10、12、14、15、16、18ppt(ng/L))提供了对某 些异味、特别是非动物衍生的蛋白质的异味的掩蔽作用。较高浓度(例如50ppt或更高(例如75ppt、100ppt、150ppt、175ppt)的添加会显著 影响一些异味属性,但还会赋予一些果味。根据消费品的不同,这些 果味是期望的或较不期望的。
术语“异味”是指在消耗消费品后随着时间的推移而产生的令人不 愉快的余味。加入环己酸乙酯会阻断、掩蔽或改变异味,并且使它们 不太明显乃至不明显。因此,非动物蛋白质将失去特别是其豆腥味、 苦味,或者至少这些异味属性将变得较不明显。
因此,在另一方面,提供了一种掩蔽包含非动物衍生的蛋白质的消费品中的异味的方法,该方法包括向所述消费品中添加有效量的环己酸乙酯的步骤。
为达到显著效果所需的环己酸乙酯的量主要取决于可食用产品中非动物衍生的蛋白的量。例如,通过向包含约3wt%的非动物衍生的蛋白质的消费品中添加至多20ppt(例如0.5ppt至约15ppt)的环己酸乙酯而获得良好的结果。作为另一个实例,可以列举人造肉消费品(例如肉片(fillets),食物块(nuggets),汉堡,香肠,“肉丸”和熟食“肉”),其包含约15-50wt%(例如17、20、25、30、35、40、45wt%)的非动物衍生的蛋白质。对于包含高含量(约15wt%至约50wt%)非动物衍生的蛋白质的此类消费品,可以添加至多250ppt的环己酸乙酯以达到良好的效果。
因此,在另一个实施方案中提供了一种消费品,其包含非动物衍生的蛋白质和环己酸乙酯,其特征在于该消费品包含至多约1ng(包括 0.005、0.01、0.05、0.1、0.25、0.3、0.5、0.5、0.75ng)环己酸乙酯/1 克非动物衍生的蛋白质。
环己酸乙酯可以直接添加到包含非动物衍生的蛋白质的消费品中,或者其可以在更早的步骤中与其他食品添加剂例如调味剂,稳定剂,乳化剂,防腐剂,树胶,淀粉,糊精,维生素和矿物质,功能性成分,盐,抗氧化剂,甜味剂和着色剂混合,或者其可以先包埋在基质材料中再混合到消费品中。
作为基质材料,可以使用任何类型的食品级载体,例如麦芽糊精 (例如,几乎无味的葡萄糖链长为19的麦芽糊精),糊精,改性淀粉,糖醇(例如甘露糖醇,山梨醇,麦芽糖醇,异麦芽酮糖),糖(例如果糖,乳糖,葡萄糖)及其混合物。
适合的调味剂的实例包括天然调味剂,人造调味剂,香料,调味料等。示例性的调味剂包括合成香味油和调味芳香剂和/或油,油树脂,精油和馏出物,以及包含前述物质的至少一种的组合。
香味油包括留兰香油、肉桂油、冬青油(水杨酸甲酯)、薄荷油(peppermint oil)、日本薄荷油、丁香油、月桂油、茴香油、桉叶油、百里香油、柏叶油、肉豆蔻油、多香果、鼠尾草油、肉豆蔻、苦杏仁油和桂皮油;有用的调味剂包括人造、天然和合成水果香精,例如香草和柠檬油,包括柠檬、橙子、来檬、葡萄柚、香橙(yuzu)、酢橘 (sudachi),和水果精油,包括苹果、梨、桃子、葡萄、覆盆子、黑莓、圆醋栗、越桔、草莓、樱桃、李子、洋李、葡萄干、可乐、瓜拉那、橙花油、菠萝、杏子、香蕉、甜瓜、杏子、樱桃、热带水果、芒果、山竹果、石榴、番木瓜等。
调味剂赋予的其他示例性香味包括牛奶香味、黄油香味、干酪香味、奶油香味和酸奶香味;香草香味;茶或咖啡香味例如绿茶香味、乌龙茶香味、茶香味、可可香味、巧克力香味和咖啡香味;薄荷香味例如薄荷香味、留兰香香味和日本薄荷香味;香辣香味例如阿魏香味、香旱芹香味、大茴香香味、当归属香味、小茴香香味、多香果香味、肉桂香味、黄春菊香味、芥茉香味、小豆蔻香味、葛缕子香味、小茴香子香味、丁香香味、胡椒香味、芫荽子香味、黄樟香味、香旱芹菜香味、川花椒香味、紫苏香味、杜松子香味、姜香味、八角茴芹香味、辣根香味、百里香香味、龙艾香味、莳萝子香味、辣椒香味、肉豆蔻香味、罗勒香味、马郁兰香味、迷迭香香味、月桂叶香味和绿芥末(日本辣根)香味;坚果香味例如杏仁香味、榛子香味、澳洲坚果属香味、花生香味、美洲山核桃香味、阿月浑子香味和胡桃香味;酒精香味例如葡萄酒香味、威士忌酒香味、白兰地酒香味、甜酒香味、杜松子酒香味和利口酒香味;花香味;和蔬菜材料例如洋葱香味、大蒜香味、甘蓝香味、胡萝卜香味、芹菜香味、蘑菇香味和蕃茄香味。
通常,可以使用任何调味剂或食品添加剂,例如National Academy of Sciences在“Chemicals Used in Food Processing”,出版号1274,第63-258页中描述的那些。该出版物通过引用并入本文。
香味组合物典型地以基于消费品0.01-2wt%(例如约0.2wt%至约 1wt%)混合至消费品中。为了获得包含至多150ppt的环己酸乙酯的消费品,此类香味组合物应包含至多1500ppb(μg/L)的环己酸乙酯。
因此,在另一个实施方案中,提供了一种适合于掩蔽非动物衍生的蛋白质的异味的组合物,该组合物包含约0.025ppb至高达约 1500ppb的环己酸乙酯和至少一种调味剂。
在一个实施方案中,可以将环己酸乙酯与另外的异味掩蔽剂和/或包含异味掩蔽剂的香味系统混合。例如,根据终产品的不同,可以增加产品的甜度或咸度以掩蔽异味,例如苦味。本领域技术人员可以通过调节终产品的pH来掩盖涩味。
在另一个实施方案中,如WO2017/037181中详细公开的,可以将环己酸乙酯与包含蛋白质结合剂的香味系统组合,该公开文献通过引用并入本文。蛋白质结合剂的定义如下:
在一个实施方案中,基于其连接或结合蛋白质的能力来选择结合剂,从而防止蛋白质与芳香剂结合。这种结合蛋白质和“释放”芳香剂的能力由许多因素决定,包括例如氨基酸性质,蛋白质确认,疏水性,加入时间,蛋白质在加工过程中的行为,特征性芳香剂的类型和芳香剂的极性。根据一个实施方案,蛋白质结合剂可以包括至少一种萜烯和至少一种羰基化合物的混合物。在另一个实施方案中,所述蛋白质结合剂可以包括萜烯和两种或更多种羰基化合物的混合物。在一个实施方案中,适合的萜烯类(类异戊二烯和四萜类化合物)包括、但不限于胡萝卜素类(例如α-胡萝卜素、β-胡萝卜素、γ-胡萝卜素、δ-胡萝卜素、番茄红素、链孢红素、六氢番茄红素、八氢番茄红素)和叶黄素 (xanthophyll)(例如角黄素、隐藻黄素、玉米黄质(aeaxanthin)、虾青素、叶黄素(lutein)、玉红黄质);单萜类(例如苧烯、紫苏子醇);倍半萜类(例如石竹烯、β-石竹烯、姜烯);皂苷类;脂质包括:植物甾醇类、菜油甾醇、β谷甾醇、γ谷甾醇、豆甾醇)、生育酚类(维生素E)和ω-3、 -6和-9脂肪酸(例如γ-亚麻酸);三萜系化合物(例如齐墩果酸、熊果酸、桦木酸、摸绕酮酸(moronic acid));α-蒎烯类、顺式-β-罗勒烯类和红没药烯类(例如α-红没药烯和γ-红没药烯)。适合的羰基化合物包括酮类和醛类,包括、但不限于丙酮、乙酰甲基甲醇、苯乙酮、2-丁酮、L- 香芹酮、D-香芹酮、二乙酰、2-庚酮、β-紫罗兰酮、L-薄荷酮、茴香基丙酮(anisyl acetaone)、甲基环戊烯醇酮、甲基壬基酮、甲基庚烯酮、 2-壬酮、2-辛酮、2-戊酮、2-十一烷酮(2-undecanonen)、4-羟基-2,5二甲基-3(2H)-呋喃酮、诺卡酮、十三烷酮、十四内酯、癸内酯、丁内酯、 2-十三烷酮、苯甲醛、正丁醛、异丁醛、肉桂醛、香茅醛、癸醛、十二烯醛(docecenal)、己醛、醛C-12、醛C-8、乙醛、反式-2-己烯醛、茴香醛、反式2-癸烯醛、顺式-3-己烯醛和顺式-4-庚烯醛。
根据本公开,术语“消费品”是指典型地通过口腔(尽管可以通过非口服方式例如吸入来消费)发生的受试者消费的产品,用于享受、营养或健康和保健福利的至少一个目的。消费品可以以任何形式存在,包括但不限于液体,固体,半固体,片剂,胶囊,锭剂,条,粉末,凝胶,树胶,糊剂,浆液,糖浆剂,气雾剂和喷雾剂。该术语还指例如饮食和营养补充剂。消费品包括在被丢弃之前放置在口腔内一段时间但不被吞咽的组合物。食用前可放入口中,或放入口中一段时间后再丢弃。
广义上,消费品包括但不限于各种食品,糖果产品,烘烤产品,甜味产品,美味产品,发酵产品,乳制品,饮料,口腔护理产品,营养制品和药品。
示例性的食品包括但不限于速冻小吃、甜和风味极佳的小吃、水果小吃、油煎土豆片/炸土豆片、膨化食品、玉米饼/玉米片、玉米花、椒盐卷饼、坚果、其他甜和风味极佳的点心、小吃、燕麦棒、早餐棒、能量棒、水果棒、其他小吃、膳食替代品、减肥产品、恢复性饮料、即食食品、罐头即食食品、冷冻即食食品、干燥即食食品、冷冻即食餐、混合方便饭(dinnermixes)、肉类同型物(meat analogues)、速冻比萨、冷冻比萨、汤、汤品罐头、汤粉、速溶汤粉、冷汤、超高温汤、冷冻汤、意面、罐装意面、干意面、冷冻/新鲜意面、面条、面条、方便面、杯装/碗装方便面、袋装方便面、凉面、方便面、干燥食品、什锦点心、酱油、调料和调味品、草药和香料调味品、糊状食品、果酱和蜜饯、蜂蜜、巧克力酱、基于坚果的酱和基于酵母的粉酱。
示例的糖果产品包括但不限于口香糖(包括糖化口香糖、不含糖的口香糖、功能性口香糖和泡泡糖)、中心填充糖食、巧克力和其他巧克力糖食、含药糖食、糖锭、片、软果糕、薄荷糖、标准薄荷糖、强力薄荷糖、耐嚼的糖、硬糖、透明硬糖(boiled candy)、呼吸和口腔护理膜或条、棒棒糖、棒糖、胶粘糖、果冻、法奇软糖、焦糖、硬和软的糖球、太妃糖、乳脂糖、甘草、明胶糖、软糖、豆形胶质软糖、牛轧糖、软糖、上述一种或多种的组合。
示例性的烘烤产品包括但不限于焦糖甜饼(alfajores)、面包、包装 /工业用面包、散装/手工艺面包、糕点、蛋糕、包装/工业蛋糕、散装/ 手工艺蛋糕、饼干、巧克力糖皮饼干、夹心饼干、夹心饼干、香味饼干和薄脆饼干、面包替代物。
示例性的甜味产品包括但不限于早点用谷物片、方便(“rte”)谷物食品、家庭早点用谷物片、薄片、穆兹利、其他方便谷物食品、儿童早点用谷物片、热谷物。
示例性的美味产品包括但不限于咸味零食(马铃薯片、炸土豆片、坚果、炸玉米粉圆饼、椒盐卷饼、干酪零食、谷粒零食、马铃薯-零食、方便食品玉米花、可微波爆裂开的爆玉米花、猪肉皮、坚果、薄脆饼干、薄脆零食、早点用谷物片、午餐/早餐人造肉(热狗、冷吃的肉片、香肠)、番茄产品、人造黄油、花生酱、汤(清汤、罐装汤、奶油汤、速溶汤粉、超高温UHT)、罐装蔬菜和意大利面调味品。
示例性的乳制品包括、但不限于干酪、干酪调味品、基于干酪的产品、冰淇淋、即兴消费的冰激凌、单份牛奶冰淇淋、单份水冻冰块冰淇淋(single portion water icecream)、一包多件包装的牛奶冰淇淋、一包多件包装的水冰激凌、带回家的冰激凌、带回家的牛奶冰淇淋、冰淇淋甜点、散装冰淇淋、带回家的水冰淇淋、冷冻酸奶、手工冰淇淋、乳制品、豆乳、咖啡白化剂、冷冻点心和耐储存点心、基于大豆的点心。
示例性的饮料包括但不限于包含蛋白质的增香水、软饮料、果汁饮料、基于咖啡的饮料、基于茶的饮料、基于果汁的饮料(包括水果和蔬菜)、凝胶饮料、碳酸或非碳酸饮料、饮料粉、酒精或非酒精饮料以及这些饮料的即饮液体制品。
示例性的发酵食品包括但不限于干酪和干酪产品、肉类和肉制品、大豆和大豆产品、鱼肉和鱼制品、谷物和谷物产品、水果和水果产品。
在某些实施方案中,提供了包括高浓度的非动物衍生的蛋白质(例如大豆蛋白、豌豆蛋白或其混合物)的饮料组合物。蛋白质的总量可以占高蛋白质饮料组合物的约2%重量至约15%重量,或约2%重量至约12%重量,或约3%重量至约10%重量,或约4%重量约8%重量,或约5%重量至约7%重量,或约6.4%重量至6.5%重量,或约6.4%蛋白质重量,或大于3%重量,大于4%重量,大于5%重量,或大于 6%重量,或在这些范围内的任何百分比范围或特定百分比。
现在参考以下非限制性实施例进一步描述本发明。这些实施例仅出于示例的目的,并且应当理解,本领域的技术人员可以做出改变和变型。
实施例1:大豆蛋白饮料
样品A(对照):大豆蛋白饮料
样品B:样品A+0.5ppt(ng/L)环己酸乙酯
样品C:样品A+15ppt(ng/L)环己酸乙酯
将样品储存在玻璃烧杯中,用封口膜封盖,并在品尝前在冷藏温度下保持3天。品尝前,立即将样品翻置几次以确保饮料均匀性。
要求一组经过训练的品尝人员使用3ml移液器分别比较参比对照样品与样品B和样品C,并提供大豆特性最受影响的注释。将结果提供在下面的表1中。
测试方法
品尝前30分钟从冰箱中取出样品。提供胡萝卜棒、酸奶油、薄脆饼干和过滤水,以确保品尝者能够充分冲洗和清洁掉样品之间的味觉。在品尝期间,要求至少10名受过训练的品尝者分别提供样品A与样品B和样品C之间相比的区别。品尝结果还被用于比较样品B与C 之间品尝者的反馈,以表明目标化合物对豆腥味、大豆味和苦味描述的潜在浓度影响。
预先由经过训练的感官小组开发的预定义属性包括在大豆蛋白的选票上,包括“豆腥味”、“大豆味”和“苦味”。感官属性和相应的定义可以在下面找到。
表1:
---掩蔽,--中度掩蔽,-轻度掩蔽
属性的感官描述:
豆腥味:与豆腐(tofu)和豆腐(bean curd)相关的白垩味、甜味、大豆样香味。
大豆味:与大豆蛋白相关的芳香味,包括蛋白质味、青香味、维生素味、豆腥味、土壤味和淀粉味。
苦味:与在水中稀释的物质例如咖啡因或奎宁相关的基本味觉。
实施例2:马铃薯蛋白
制备包含3重量%的马铃薯蛋白质(Avebe的SolanicTM 200)的马铃薯蛋白质水溶液(样品A)。尽管样品A被描述为土壤味、发霉味、鱼腥味、苦味,但添加了14ppt环己酸乙酯的样品被描述为土壤味、马铃薯味,但没有注意到鱼腥味、苦味属性。
实施例3:豌豆蛋白
样品A(对照):豌豆蛋白饮料
样品B:样品A+15ppt(ng/L)环己酸乙酯
样品C:样品A+30ppt(ng/L)环己酸乙酯
将样品储存在玻璃烧杯中,用封口膜封盖,并在品尝前在冷藏温度下保持三天。品尝前,立即将样品翻置几次以确保饮料均匀性。
样品A被描述为土壤味、发霉味、青香味和涩味。相比之下,样品B显示土壤味、发霉味、青香味和涩味特性较低,而在样品C中甚至大幅度降低,尤其是对于土壤味、发霉味和涩味的感觉。
实施例4:素食肉丸(肉替代品)
表2:
(1)Du Pont的Solae Supro XT 291D
(2)Bob’s Red Mill的Bob’s Red Mill Vital Wheat Gluten 75-80% Protein
(3)Du Pont的Response 4310IP
*如WO2017/037181中定义的包含0.32wt%蛋白质结合剂的改性淀粉
**进一步包含15ppb环己酸乙酯(导致终产品中的终浓度为约 0.18ng/g蛋白质)的组合物A
基于上述表2的配方制备肉丸如下。
将水与大豆片一起添加到Thermomix中,并在室温下混合。10 分钟后,在混合的同时添加大豆蛋白分离物和小麦面筋。同时打开加热器至100℃,并且混合各成分直至达到设定温度100℃,并持续1分钟。
取出组合物并形成1oz(约28g)的球。将如此制备的球罐装以便储存。
样品评价:
打开罐并将其倾入单独的小罐中,并在带有铝箔的罐盖中的介质上加热,直到内部肉丸球温度达到165F(约74℃)。肉丸由8-10位经过训练的小组成员进行评价,他们被要求描述样品A与对比物之间以及样品A与样品B之间的区别。结果如下表3中所示。
表3:
使用从无效果(±)到最佳效果(+++++)的等级对总体性能进行评级从未注意到(0)到非常强烈(5)的等级对味觉描述进行评级
正如从上述结果中可以观察到的,与大豆蛋白相关的豆腥味、大豆味和苦味异味被包含环己酸乙酯的掩蔽剂组合物掩蔽/阻断。
Claims (6)
1.消费品,包含非动物衍生的蛋白质和至少0.001ng环己酸乙酯/1克非动物衍生的蛋白质。
2.权利要求1的消费品,包含至多1ng环己酸乙酯/1克非动物衍生的蛋白质。
3.掩蔽包含非动物衍生的蛋白质的消费品中的异味的方法,包括向该消费品中添加有效量的环己酸乙酯的步骤。
4.用于掩蔽非动物衍生的蛋白质异味的掩蔽组合物,包含环己酸乙酯。
5.权利要求4的掩蔽组合物,包含至多1500ppb的环己酸乙酯和至少一种调味剂。
6.权利要求4或权利要求5的掩蔽组合物,包含至少0.025ppb的环己酸乙酯。
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US201862677365P | 2018-05-29 | 2018-05-29 | |
US62/677,365 | 2018-05-29 | ||
PCT/EP2019/063604 WO2019228957A1 (en) | 2018-05-29 | 2019-05-27 | Organic compounds |
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BR112022018871A2 (pt) * | 2020-03-26 | 2022-11-22 | Ajinomoto Kk | Agente e método para mascarar um cheiro desagradável de um produto oral, e, método para produzir um produto oral no qual um cheiro desagradável é mascarado |
MX2024002759A (es) | 2021-09-10 | 2024-03-22 | Unilever Ip Holdings B V | Analogo de carne y metodo para disminuir el sabor desagradable del mismo. |
TWI789235B (zh) | 2022-02-09 | 2023-01-01 | 金寶電子工業股份有限公司 | 品酒用載體組、品酒載體及品酒載體的製造方法 |
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EP3801048A1 (en) | 2021-04-14 |
JP7474708B2 (ja) | 2024-04-25 |
CO2020016266A2 (es) | 2021-01-18 |
BR112020022868A2 (pt) | 2021-02-23 |
JP2021526021A (ja) | 2021-09-30 |
MX2020011825A (es) | 2021-01-15 |
US20210204580A1 (en) | 2021-07-08 |
CN112638170B (zh) | 2024-04-12 |
PE20211387A1 (es) | 2021-07-27 |
WO2019228957A1 (en) | 2019-12-05 |
CA3101206A1 (en) | 2019-12-05 |
SG11202010989XA (en) | 2020-12-30 |
CL2020003037A1 (es) | 2021-06-11 |
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