1. Chapter Lipids (类脂)
Ref: Wade, chapter 25

2. Lipids are compounds that can be extracted from cells and tissues by nonpolar organic solvents.
Waxes: 蜡
Complex lipids
Fats and oils 油脂: glycerides
phospholipides: 磷脂
Steriods 甾体
Simple lipids
Terpenes 萜
Prostaglandins 前列腺素

3. Waxes
Most waxes are esters of long-chain fatty acids and long-chain alcohols.
Waxes are found as protective coatings on the skin, fur, or feathers of animals, and on the leaves and fruits of plants.
spermaceti 鲸蜡
beeswax
蜂蜡的一种
Notice: parafin wax (石蜡) is a mixture of alkanes with high molecular weight。

4. 19-2 Triglycerides 三酸甘油酯 （25-3, 4）
Oils: Triacylglycerols that are liquids at room temperature.
Fats: Triacylglycerols that are solids at room temperature.
The primary function of triacylglycerols in animal is as an
energy reserve.

5. Common naturally occurring fatty acids
月桂酸
肉豆蔻酸
软脂酸
硬脂酸
花生酸

6. 棕榈油酸 油酸
亚油酸
亚麻酸
花生四烯酸

7. A fat
An oil

8. ① Most of fatty acids have unbrached chains and they have an even number of carbon atoms.
② The double bonds in unsaturated fatty acids are all cis and not conjugated..
③ Saturated fatty acids have relatively high melting points and unsaturated fatty acids have relatively low points.
Saponification reaction: soaps
Synthetic detergents

9. Synthesis of detergents offer an advantage over soaps; they
function well in “hard” water.

10. 19-3 Phospholipids 磷脂 （25-5） a phosphatidic acid 磷脂酸
hydrophobic portion
hydrophilic portion

11. Phosphoacylglycerols form membranes by arranging
themselves into a lipid bilayer

12. 19-4 Terpenes 萜类 Terpenes contain carbon atoms in multiples of five
They are made by joining together 5-carbon isoprene
units
The Isoprene Rule
异戊二烯规则

13. Classification of terpenes单萜 三萜
倍半萜 四萜 双萜
monoterpenes

14. triterpenes
squalene 角鲨烯

15. Lycopene (番茄红素)
b-carotene（胡萝卜素）
tetraterpenes

16. Vitamin A

17. The biosynthesis of terpenes:

19. Steroids (甾体)

20. The A and B rings are also trans fused in most naturally
occurring steroids
Substituents on the same side of the steroid ring system as the angular methyl groups are b-substituents
Those on the opposite side of the plane of the ring
system are a-substituents

21. Cholesterol 胆固醇
Cholesterol is known to serve as an intermediate in the biosynthesis
of all of the steroids of the body.

22. Biosynthesis of Cholesterol
角鲨烯
（三萜）
羊毛甾醇
羊毛甾醇
（三萜）
胆固醇

23. conrotatory 顺旋
7-脱氢胆甾醇
[1,7] σ-迁移

26. 19-6 Prostaglandins 前列腺素 Structure: C20-carboxylic acids
a five-membered ring,
at least one double bond,
several oxygen-Containing functional groups.

27. The biosynthesis of prostaglandins of the 2 series begins with a
C20 polyenoic acid, arachidonic acid.