油脂的结构.pptx

结构和命名物理性质化学性质1.概述 脂类的定义 能溶于有机溶剂如醚、氯仿、丙酮、苯等，不溶或微溶于水的有机化合物。脂类和碳水化合物及蛋白质共同构成了生物细胞的主要结构组分。主要有脂肪（三酰基甘油），衍生化合物（磷脂、糖脂）、类固醇及类胡萝卜素 脂类的功能l 营养 l 生物生理l 食品品质-颜色-质构-细滑,柔软 -风味-饱腹感l 分类分类groups sub-groupcomposition简单脂类甘油酯甘油酯脂肪酸+甘油蜡脂肪酸+alcohols(醇醇)复合脂类phospholipides(phosphatides)(磷脂磷脂)脂肪酸脂肪酸+甘油甘油+phosphoric acid(磷酸磷酸),+其它含氮的基团glycolipids(糖脂糖脂)脂肪酸+甘油+碳水化合物其它sphingolipids(鞘脂鞘脂)and sulfolipids(硫脂硫脂)衍生脂类fatty acids(脂肪酸脂肪酸)醇高碳醇and sterols(固醇固醇)Hydrocarbons(烃烃)-Bloor,1925monoglyceridewax简单脂类三甘酯单甘酯蜡复杂脂类phospholipidglyceroglycolipidsphingolipid磷酯糖酯鞘酯衍生脂类脂肪酸脂肪酸固醇固醇烃(beta-胡胡萝卜素卜素)2 结构和命名 2.1 简单脂类2.1.1 脂肪酸carboxyl end(羧基端羧基端)methyl end(甲基端甲基端)2.1.1.1 脂肪酸结构CH3CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2CH2 COOH偶数碳 直链无分支 碳链含 4 to 24 碳原子methylene(亚甲基)CH3(CH2)14 COOHPalmitic acid(棕榈酸)saturated (饱和的)monounsaturated (单不饱和的)polyunsaturated (多不饱和的)CH3(CH2)5CH=CH(CH2)7COOHpalmitoleic acid(棕榈油酸)CH3(CH2)4 CH=CH CH2CH=CH(CH2)7COOHlinoleic acid(亚油酸)双键 cis configuration (顺式构型)trans configuration (反式构型)C=C棕榈油酸(cis)CH3(CH2)5(CH2)7COOHHHC=C棕榈油酸(trans)CH3(CH2)5(CH2)7COOHHH硬脂酸油酸COHOStearic acid(硬脂酸)Oleic acid(油酸)Elaidic acid(反油酸)Conjugated(共轭亚油酸）亚甲基共轭linoleic acidconjugated linoleic acid异构体1012-ability to inhibit cancer-ability to lower blood cholesterol-ability to reduce body fat and increase lean muscle massIn July 2008,CLA is generally recognized as safe by FDA for certain food categories,including fluid milk,yogurt,meal replacement shakes,nutritional bars,fruit juices and soy milk 2.1.1.2 脂肪酸的命名饱和hexadecane(十六烷烃十六烷烃)hexadecanoic(十六酸十六酸)CH3(CH2)14COOH 系统命名法 普通名称或俗名：棕榈酸 缩写:16:0 符号:P不饱和脂肪酸 一双键:CH3(CH2)5CH=CH(CH2)7COOHhexadecene(十六烯烃十六烯烃)hexadecenoic(十六烯酸十六烯酸)两个双键:-dienoic octadecadienoic(十八二烯酸十八二烯酸)三个双键:-trienoic octadecatrienoic(十八三烯酸十八三烯酸)CH3(CH2)7CH=CH(CH2)7COOH 双键位置 geometrical configuration(几何构型几何构型)系统命名:cis-9-octadecenoic(9-octadecenoic)(顺顺-9-十八烯酸十八烯酸)俗名:油酸 缩写:18:1(9c)符号:O不饱和脂肪酸18,7,6,5,4,3,29 编号从碳链的甲基端开始，或或 n-不饱和脂肪酸-另一种命名方式CH3(CH2)4 CH=CH CH2CH=CH(CH2)7COOH cis-9,cis-12-octadecadienoic(顺顺-9,顺顺-12-十八二烯酸十八二烯酸)亚油酸,L18:2(9c,12c)cis 构型双键被亚甲基隔开12,3,4,5618:2 6(n-6)3 fatty acids -亚麻酸:植物种子 -EPA(20:5 3):fish oil -DHA(22:6 3):fish oil 6 脂肪酸 9 脂肪酸不饱和脂肪酸Practice:CH3CH2 CH=CHCH2CH=CH CH2CH=CH(CH2)7COOHLinolenic acid(亚麻酸),Ln系统命名?缩写:and?食品中脂肪酸的命名缩写 系统名称俗名符号4:0丁酸Butyric(丁酸丁酸)B6:0几酸Caproic(己酸己酸)H8:0辛酸Caprylic(辛酸辛酸)Oc10:0癸酸Capric(癸酸癸酸)D12:0Dodecanoic(十二酸十二酸)Lauric(月桂酸月桂酸)La14:0Tetradecaboic(十四酸十四酸)Myristic(肉豆蔻酸肉豆蔻酸)M16:0Hexadecanoic 十六酸Palmitic棕榈酸P16:1(n-7)9-Hexadecenoic 9-十六烯酸Palmitoleic 棕榈油酸Po18:0Octadecanoic 十八酸Stearic(硬脂酸硬脂酸)St18:1(n-9)9-Octadecenoic 9-十八烯酸Oleic 油酸O18:2(n-6)9,12-Octadecadienoic 9，12十八碳二烯酸Lin 亚油酸oleicL18:3(n-3)9,12,15-Octadecatrienoic(十八三烯酸十八三烯酸)Linolenic(亚麻酸亚麻酸)LnAbbreviation Systematic nameTrivial nameSymbol 20:0Eicosanoic(二十酸二十酸)Arachidic(花生酸花生酸)Ad20:4(n-6)5,8,11,14-Eicosatetraenoic(二十碳四烯酸二十碳四烯酸)Arachidonic(花生四烯花生四烯酸酸)An20:5(n-3)5,8,11,14,17-Eicosapentanoic(二十碳五烯酸二十碳五烯酸)EPA22:1(n-9)Erucic acid(13-二十二烯酸二十二烯酸)(芥子酸芥子酸)22:6(n-3)4,7,10,13,16,19-Docosahexanoic(二十二碳六烯酸二十二碳六烯酸)DHA 短链脂肪酸:10 C 中等链长的脂肪酸:12C-14C 长链脂肪酸:16C常见脂肪或油的脂肪酸组成milk fatLard猪油cocoa butter可可脂可可脂coconut oil椰子果椰子果palm oil棕榈油cottonseed oil棉籽油peanut oil花生油sesame oil 芝麻油芝麻油soybean oil大豆油cod liver oil 鳕鳕鱼肝鱼肝油油lactic 6:08:010:012:014:014:115:016:016:117:02.8-4.01.4-3.00.5-1.71.7-3.22.2-4.55.4-14.60.6-1.626-412.8-5.70.110.30.526-322-524481790.5-632-450.5-1.520-230-16-90-1.77-982.40.211.97.80.5milk fatLard猪油cocoa butter可可脂可可脂coconut oil椰子果椰子果palm oil棕榈油cottonseed oil棉籽油peanut oil花生油sesame oil 芝麻油芝麻油soybean oil大豆油cod liver oil 鳕鳕鱼肝鱼肝油油18:018:118:218:318:420:020:120:220:420:522:022:122:422:522:624:06.1-11.218.7-33.40.9-3.712-1641-573-140-10-135382.12712-738-525-111-323-3542-540.2-1.53-653-7113-272-41-34-5537-4935-474285362.826.31.50.61.310.91.56.26.91.412.4 长链脂肪酸数量最多 牛奶中含有较多的4-12C脂肪酸椰子油中主要含12 和 14 C脂肪酸 可可脂:16:0,18:0,18:1 98%植物油:亚油酸 大豆油:亚麻酸b鱼油:EPA,DHA 结论 2.1.2 Acylglycerol(酰基甘油)(甘油酯)2.1.2.1 结构2+单酰基甘油2 H2OTriacylglycerol(三酰甘油)酯键 脂肪酸和甘油形成酯甘油HO三酰基甘油结三酰基甘油结构构 CH2O OCH CH2O OC(CH2)nCH3H3C(CH2)nCO OC(CH2)nCH3HHHOHHOMG monoglycerideDG diglycerideTG Triglyceride饱和Food fats and oils单不饱和多不饱和椰子油可可脂乳脂猪油棕榈油橄榄油(低酸菜籽油)Sunflower oilSafflower oil(红花籽油)Corn oilCotton oilSoybean oilLinseed oil(亚麻籽油)Fish oil 甘油三酯中的脂肪酸的链长和饱和程度可各不相同，决定了脂肪酸的物理和化学性质 单甘酯和二甘酯1-棕榈酸-2-油酸甘油酯 glycerol monostearate(甘油单硬脂酸酯)Emulsifier(乳化剂)2.1.2.2 命名Stereospecific numbering(立体定向编号立体定向编号)-sn(IUPAC-IUB)系统命名112233 系统名称 CH2OOC(CH2)14CH3 CH3(CH2)7CH=CH(CH2)7COOCH CH2OOC(CH2)16CH3 1-palmitoyl-2-oleoyl-3-stearoyl-sn-glycerol 缩写:sn-16:0-18:1-18:0 符号:sn-POSt (-ic -oyl)1-棕榈酰棕榈酰-2-油酰油酰-3-硬脂酰硬脂酰-sn-甘油甘油)POSt sn-POSt sn-PStOsn-OStPsn-OPStsn-StOPsn-StPOmixture of 6 triacylglycerols练习题:C18:3 3 sn-StLP 2.1.2.3 脂类中脂肪酸的分布 分布理论-完全随机-1,3-随机-2-随机理论-1-随机-2-随机-3随机理论天然的脂肪是酰基甘油的混合物OOO:2.7%LOL:0.096%PLSt:10.8%O 30%L 60%P 8%St 2%64(n3)Example:triacylglycerol-Completely randomized distribution:Positional distribution of FA in glyceride for some natural fats and oils Fats and oilsposition6:08:010:012:014:016:018:018:118:218:3椰子油12310.33423245133978382988161130.50.5433-22可可脂12334237502531287919-corn123182143-3128275250701soybean123141136-6232228487045978Unit:mol%position6:08:010:012:014:016:018:018:118:218:3olive123131173-4728374101450.60.81peanut123142115-5595957193910牛油depot fat12341172217924204137455111猪油(back)1231072-30275113736318Positional distribution of FA in glyceride for some natural fats and oils Fats and oilsposition6:08:010:012:014:016:018:018:118:218:3coconut12310.33423245133978382988161130.50.5433-22cocoa butter12334237502531287919-corn123182143-3128275250701soybean123141136-6232228487045978Unit:mol%结论脂肪酸的位置排布 植物:不饱和脂肪酸优先在sn-2 位置，饱和脂肪酸在sn-1 and sn-3 位置 多数动物脂肪:16:0 在sn-1 位置.而猪脂中16:0 在sn-2位置2.2 复合脂类2.2.1 磷脂Phosphoglyceride(磷酸甘油酯)非极性极性saturated FAunsaturated FA取代基团Phosphatidylcholine(磷脂酰胆碱)Phosphatidylethanolamine(乙醇胺)Phosphatidylserine(丝氨酸)Phosphatidylinositol(肌醇)CH2OOC(CH2)16CH3 CH3(CH2)4 CH=CH CH2CH=CH(CH2)7COOCH CH2OPO(CH2)2N(CH3)3 O+1-stearoyl-2-linoleoyl-sn-glycero-3-phosphocholine (1-硬脂酰硬脂酰-2-亚油酰亚油酰-sn-甘油甘油-3-磷酸胆碱磷酸胆碱)O-PhosphatidylcholineLecithin(卵磷脂卵磷脂):主要成分是磷脂酰胆碱emulsifier2.2.2(糖糖脂脂)(甘油糖脂甘油糖脂)(鞘糖脂鞘糖脂)糖脂2.2.3 鞘脂(鞘鞘氨醇氨醇)(脑脑氨氨/神经酰胺神经酰胺)(鞘磷脂鞘磷脂)(鞘糖脂鞘糖脂)2.3 衍生脂类2.3.1 固醇Stigmasterol(豆甾烯醇)(谷固醇)(胆固醇)cholesterol is essential for maintenance of life and normal functions in the human body-细胞膜的组分-precursor for synthesis of bile acid(胆酸)and steroid hormones (类固醇荷尔蒙)每日的膳食推荐摄入量是300mg