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©anna_t@flickr triglycerides g.j.rowlands unit four part 5
56

Triglycerides

Jun 12, 2015

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Education

Gareth Rowlands

A lecture I almost had to give as a 'stand-in' for one of my colleagues. Probably the fastest I've ever prepared a lecture and the first time I have taken someone else's notes and effectively given them a 'presentation make-over. Never did give it but it seems pointless having it sitting around on my hard drive.
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Page 1: Triglycerides

©anna_t@flickr

triglycerides

g.j.rowlandsunit four part 5

Page 2: Triglycerides

fats

can

taste...©*Micky@flickr

Page 3: Triglycerides

good!©Mrs Magic@flickr

Page 4: Triglycerides

providemore energy

than carbohydrate or protein

©swisscan@flickr

Page 5: Triglycerides

but...

Page 6: Triglycerides

is notvery

good forus

©Pixar / Disney

Page 7: Triglycerides

O

O

O

O

O

Otriglycerides

Page 8: Triglycerides

OH

OH

OH

glycerol

triglycerideformation

Page 9: Triglycerides

triglycerideformation

OH

OH

OH 3 xHO

O

R

glycerol fatty acid

Page 10: Triglycerides

triglycerideformation

OH

OH

OH 3 xHO

O

R

O

O

O

O

O

R

R

O

R

glycerol fatty acid

triglyceride

Page 11: Triglycerides

natural fats and oils

©Shereen M (away)@flickr

Page 12: Triglycerides

fatty acids

HO

O

myristic acid©JustABigGeek@flickr

Page 13: Triglycerides

HO

O

oleic acid

fatty acids

Page 14: Triglycerides

fatty acids

HO

O

linolenic acid©Chris & Lara Pawluk@flickr

Page 15: Triglycerides

©Thomas Hawk@flickr

HO

O

saturatedfat

Page 16: Triglycerides

©darwin bell@flickr

unsaturated

fat

HO

O

Page 17: Triglycerides

©Marco Veringa@flickr

HO

O

polyunsaturated

fat

Page 18: Triglycerides

HO

O

alwayscis-alkenes

Page 19: Triglycerides

HO

O

©cultr.sun@flickr

acidstrans-fatty are processed

Page 20: Triglycerides

CO2H

saturatedchains

Page 21: Triglycerides

pack wellCO2H

saturatedchains

Page 22: Triglycerides

solids

highmelting points

©niznoz@flickr

Page 23: Triglycerides

unsaturatedchains

kinked

CO2H

Page 24: Triglycerides

CO2H

unsaturatedchains

kinked

don’t

Page 25: Triglycerides

oils

lowmelting points

©☻mrhappy☻@flickr

Page 26: Triglycerides

reactions

©euthman@flickr

Page 27: Triglycerides

HO

O

Br Br

HO

O BrBr

additionreactions

Page 28: Triglycerides

HO

O

H Hmetal

catalyst

HO

O HH

hydrogenation

Page 29: Triglycerides

HO

O

H Hmetal

catalyst

HO

O HH

hydrogenation

saturated

unsaturated

Page 30: Triglycerides

©NontrivialMatt@flickr

synthesis of

margarine

Page 31: Triglycerides

R1

O

OR2

NaOH

R1

O

O NaHO R2

hydrolysisester

saponification

Page 32: Triglycerides
Page 33: Triglycerides

O

O

O

O

O

ONaOHH2O

OH

OH

OHO

O

Na

3 x

hydrolysisester

Page 34: Triglycerides

O

O

Na

soap

Page 35: Triglycerides

how does

soapwork?

Page 36: Triglycerides

O

O

Na O

O

Na

polar non-polarhydrophilic hydrophobic

Page 37: Triglycerides

micelle

hydrophobic

pocket

Page 38: Triglycerides

micellecarboxylate

hydrophilic

interactswith water

ion-dipoleinteractions

Page 39: Triglycerides

grease / dirt

hydrophobic

Page 40: Triglycerides

micelle non-polarhydrophobicportion inside

away from water

Page 41: Triglycerides

detergents

polarhydrophilic

head

non-polarhydrophobic

tail

Page 42: Triglycerides

detergentsynthesis of a

H2SO4

HO3S NaOH

O3SNa

electrophilicaromatic substitution

Page 43: Triglycerides

acidstronger

robustmore

©fdecomite@flickr

Page 44: Triglycerides

SO

O

OO

detergentanionic

Page 45: Triglycerides

N

Cl

N

detergentcationic

Page 46: Triglycerides

©AJC1@flickr

detergentcationic

N

Cl

germicidal

Page 47: Triglycerides

metabolismfatty acid

Page 48: Triglycerides

hydrolysis1

O

O

O

O

O

O

OH

OH

OHO

O3 x

your belly

Page 49: Triglycerides

metabolism2O

O

CoA-SH(coenzyme A) esterification

S

OCoA

dehydrogenation H H

S

OCoA

Page 50: Triglycerides

metabolism2

S

OCoA

hydration H2O

S

OCoA

H

OH

oxidation H H

S

OCoA

O

Page 51: Triglycerides

metabolism2

S

OCoA

O

CoA-SH(coenzyme A)

C–C splitting

S

OCoA

O

SCoA

Page 52: Triglycerides

repeatand

©estherase@flickr

Page 53: Triglycerides

©laverrue@flickr

C Henergyfrom breakingbonds

Page 54: Triglycerides

HO

O

HO

O

moreC–Hthan

Page 55: Triglycerides

©Great Beyond@flickr

storesfat

energy2 x

of sugar

Page 56: Triglycerides

thankstoTrevor Kitson