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Flashcards in chem lab - lipids Deck (103):
1

hydrophobic isoprenoids

A, D, E, K

2

are PUFAs
-must be provided in our diet because EFAs cannot be biosynthesized

EFAs

3

1. Fatty-acid related :

fatty acid/prostaglandins, fatty acid esters, sterol esters, lipoconjugates

4

2. Hydrolyzable/saponifiable:

fatty acid esters, sterol esters, lipoconjugates

5

-aliphatic, acyclic, unbranched

fatty acids

6

fatty acid synthesis in humans:

liver and lactating mammary glands

7

most naturally occurring FA contain odd or even no. of C atoms

EVEN

8

-no C=C
-CnH2n+1 COOH
-___anoic acid

saturated

9

-CnH2n-1COOH
- ____enoic acid

unsaturated

10

– natural configuration of C=C

Cis configuration

11

-introduces a kink, allowing a bend
-bend disrupts alignment of lipid → semi-fluid

Cis configuration

12

2 EFAs to humans

1. Linoleic acid –
2. Linolenic acid

13

precursor of arachidonic acid

linoleic

14

– precursor of PGs
-becomes essential if linoleic acid is missing

Arachidonic acid

15

– alkali salts of Fa
-formed by saponification
-amphipathic
-nonpolar + dirt, polar + water (micelle)

4. Soaps

16

5. Halogens add to C=C via

AE

17

– resistant to oxidation outside the body

saturated FA

18

slowly but spontaneously oxidized by oxygen in air
-becomes rancid (formation of short chain aldehydes)

USFA-

19

-derived from linoleic acid (or arachidonic acids) forming eicosanoids

PROSTAGLANDINS

20

-cyclopentane ring, 2 side chains, carboxyl group in one side chain

PROSTAGLANDINS

21

-participate in wound-healing process

PROSTAGLANDINS

22

PAIN MEDIATORS

PROSTAGLANDINS

23


-esters formed between a fatty acid (CA) and glycerol (trihydric alcohol)

Acyglycerols or glycerides

24

-3 Fatty acids + glycerol

TRIGLYCERIDES

25


-neutral fats or neutral oils

TRIGLYCERIDES

26

-most widespread

TRIGLYCERIDES

27

-most abundant lipids in animals (function: food store)

TRIGLYCERIDES

28

Hydrolysis of tripalmitin or 1,2,3-tripalmitoyl-sn-glycerol

• 1 mole of glycerol
• 3 moles of palmitic acid

29

Hydrolysis of palmitostearoolein or 1-palmitoyl-2-stearoyl-3-oleoyl-sn-glycerol

• 1 mole glycerol
• 1 mole palmitic acid
• 1 mole stearic acid
• 1 mole oleic acid

30

Hardening of oils is due to what reaction

-hydrogenation of C=C → saturated compounds

31

Drying oils s due to what reaction

-action of O2 in air forms hydroperoxides

32

-composed of an alcohol + diacylgycerol or sphingosine

phospholipids

33

-phospholipids with glycerol

phosphoglycerides/glycerophosphatides/phosphoacylglycerol

34

all phosphoglycerides contain

phosphatidic acid

35

backbone of phosphoglycerides

phosphatidic acid

36

– alcohol-soluble, acetone-insoluble

lecithin

37

-most abundant phosphoglyceride

lecithin

38

-white waxy substance
-used as an emulsifier
-predominantly phosphatidyl choline

lecithin

39

4nry amine alcohol

Choline-

40

Hydrolysis of lecithin

• 2 moles FA
• 1 mole phosphoric acid
• 1 mole choline
• 1 mole glycerol

41

– alcohol-insoluble, acetone-insoluble
-abundant in nerve and brain tissues
-mixture of phosphatidyl ethanolamine (predominant) or phosphatidyl serine

Cephalin

42

Hydrolysis of cephalin

• 1 mole ethanolamine or serine
• 2 moles FA
• 1 mole phosphoric acid
• 1 mole glycerol

43

- derivatives of perhydrocyclopentanophenanthrene

steroids

44

true terpenes

steroids

45

-synthesized in living systems from isoprene via squalene

steroids

46


-steroids with one or more OH groups (alcohols)

Sterols

47

– 27 C atoms
-2ndary alcohol

cholesterol

48

-derived from B-squalene (triterpene)

cholesterol

49

-major constituent of gallstone from which it was first isolated

cholesterol

50

-major sterol in animal tissues

cholesterol

51

1. Component of cell membrane
2. Precursor of bile acids, steroid hormones, vitamin D

cholesterol

52

– plays a central role in regulation of body’s cholesterol

Liver

53

– plasma cholesterol in esterified form
-hydrolysable

Cholesteryl esters

54

-hydrolysis of cholesteryl esters

1 mole cholesterol, 1 mole FA

55


-control 2o sex characteristics, reproductive cycle, growth and development of accessory reproductive organs

1. Sex hormones

56

produces testosterone (androgen that stimulates spermatogenesis and development of male 2o characteristics) in Leydig cells, stimulated by LH

-testis

57

produce estrogen (menstrual cycle, 2o sex characteristics) and progesterone (secretory phase of uterus and mammary glands, nidation, maturation of fertilized ovum)

-ovaries:

58


-control water and electrolyte balance, carbohydrate and protein metabolism

2. Adrenocorticoid hormones

59

secreted when ACTH is stimulated
-increased gluconeogenesis, anti-inflammatory action, protein breakdown

Cortisol –

60


-secretion induced by Na/K ratio and by angiotensin
-function: stimulates renal reabsorption of Na and excretion of K

Aldosterone

61

3. Vitamin D – lipid soluble, nonpolar, hydrophobic
-derived from isoprenoids or terpenoids

vit D

62

Vit D2

ergocalciferol

63

Vit D3

cholecalciferol

64

-most toxic of all vitamins, slowly metabolized

vit D

65

watery mixture of organic and inorganic compounds, contain lecithin and bile salts

-Bile:

66

pKa = 6, not fully ionized

bile acids

67

provide the only mechanism for cholesterol excretion

bile salts

68

emulsifier

bile acids, soap, lecithin

69


-multiples of isoperene units
-where most of the plant’s pleasant odors come from

TERPENOIDS OR ISOPRENOIDS

70

– a triterpene
-precursor of cholesterol
-all trans-configuration

Squalene or β-squalene

71

-collective term for retinol, retinoic acid, retinal, β-carotene (tetraterpene)
-found in green vegetables, fruits, eggs
-stored in liver

vit A

72

-function: essential for vision, growth and reproduction
-deficiency: night blindness, xerophthalmia

vit A

73

– visual pigment consisting of retinal and opsin

Rhodopsin

74

rhodopsin consists of (2)

retinal and opsin

75


-found in vegetable oils, egg
-naturally occurring tocopherols

Vitamin E

76

most active tocopherol

alpha-tocopherol

77

-function: natural antioxidant

Vitamin E

78

-least toxic of fat-soluble vit

Vitamin E

79


-in cabbage, cauliflower, spinach, egg yolk
-stored in liver
-absorbed in presence of bile acid

Vitamin K

80

parent cpd of Vitamin K

menadione, vit K3

81

-function: Koagulations vitamin
-large doses: haemolytic anemia, jaundice

VIT K

82


-first isolated from the brain

SPHINGOLIPIDS

83

-2nd most abundant class of lipids

SPHINGOLIPIDS

84

-found in cell membrane of nerve and brain tissues

SPHINGOLIPIDS

85

-backbone compound of sphingolipids

ceramide

86

phospholipids with sphinosine

Sphingosine Phosphatides –

87

– abundant in brain and nerve tissues
-zwitterionic, amphipathic

Sphingomyelin

88

– accumulation of sphingomyelin in large amounts in brain, liver, spleen

Niemann-Pick disease

89

Hydrolysis of sphingomyelin:

1 mole fatty acid
• 1 mole sphingosine
• 1 mole phosphoric acid
• 1 mole choline

90


-sphingolipids with carbohydrates, without phosphorus
-primary OH group is hydroxylated

Sphingosine glycosides or glycosphingolipids

91

sphingolipid found in white matter of brain

Cerebroside or galactosyl ceramide –

92

– glucose replaced galactose

Gaucher’s disease

93

Hydrolysis of cerebrosides

• 1 mole of D-galactose
• 1 mole sphingosine
• 1 mole FA

94

– also found in brain
-OH of C3 is esterified to a sulphate group

Cerebroside sulfates/Sulfatides

95

– glycosphingolipids with sugar sialic acid

Gangliosides

96

number of grams of I2 absorbed by 100 g lipid sample

Iodine number-

97

– number of mg KOH needed to neutralize free fatty acids or fatty acids released as result of hydrolysis in 1 g lipid sample or fatty acid released

Acid Value

98

-↑ acid number, ______

↑tendency to be rancid

99

-measure of acidity, measure of the tendency to become rancid

Acid Value

100

– number of mg KOH required to saponify the ester in 1 g of lipid sample

Ester Number

101

Acid Number + Ester Number =

Saponification Number

102

number of mg KOH required to neutralize free fatty acids or fatty acids released as a result of hydrolysis and to saponify esters contained in1g lipid sample

Saponification Number-

103

-lipid constant also called Koetts Dorfer

Saponification Number-

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