BIOCHEMLEC LIPIDS s2

Carboxylic acid, carboxyl group, hydroxyl

-contains a - which consists of a --OH attached to the carbon in a carbonyl group.

Methanoic acid

A red ant sting contains - (formic acid) that irritates the skin

Ethanoic scid

The sour taste of vinegar is due to _ (acetic acid).

Carboxylic acid

can be prepared from primary alcohols or aldehydes

Carboxylic acid

can be produced from the oxidation of primary alcohols to aldehydes and then to carboxylic acids

Alpha hydroxy acid AHAS

are naturally occurring carboxylic acids with a hydroxyl group on the carbon atom that is adjacent to the carboxyl group

AHAS

are found in fruits, milk, and sugar cane

AHAS

Several different - may be found in skin care products singly or in combination

Polarity of carboxylic acid

Strongly polar due to two polar groups

Dimers

The higher boiling points of carboxylic acids can also be attributed to the formation of — between two carboxylic acids.

Carboxylic acid

form hydrogen bonds with many water molecules.

Carboxylic acid, 1-5, very soluble

with one to five carbon atoms are very - in water

Increases,

are less soluble as the number of carbons -

Carboxylic acid

are weak acids

Carboxylate ions, hydronium

dissociate in water to produce — ions and — ions.

Proton, 2

can lose a - because - oxygen atoms in a carboxylate ion stabilize negative charge

Carboxylate salt

are a product of the neutralization of a carboxylic acid with a strong base such as NaOH or KOH.

Esters

synthesized from the reaction of a carboxylic acid and alcohol.

Esters

found in fats and oils

Esterification

the replacement of the hydrogen atom in the carboxylic acid -OH group with an alkyl group from an alcohol

Aspirin

In 1899, the Bayer chemical company

produced an ester of salicylic acid and acetic acid less irritating to the stomach than salicylic acid.

ester acetylsalicylic acid

called the - (aspirin).

Methyl salicylate

Oil of wintergreen,

Esters

Boiling point is Lower than alcohols and carboxylic acid

Esters

Higher than hydrocarbons

Higher boiling point= higher imfa

-bp -imfa

Two five

Esters are soluble if they have - to - carbon atoms.

Decrease

As the number of carbons increases from five, their solubility in water -

Negative , positive

The partially - oxygen of the carbonyl group forms hydrogen bonds with the partially - hydrogen atoms of water molecules.

Acid hydrolysis of esters

an ester reacts with water to produce a carboxylic acid and an alcohol.

-oh group, hydrolysis of esterd

a water molecule provides an - group to convert the carbonyl group of the ester to a carboxyl group

Acid catalyst, heat

In acid hydrolysis

an - and - are required.

Base hydrolysis (saponification)

is the reaction of an ester with a strong base in the presence of heat.

Base hydrolysis (saponificatiin)

produces a carboxylate salt and an alcohol.

Lipids

named from the Greek word lipos, which means "fat."

Lipids

biomolecules that contain fatty acids or a steroid nucleus

Lipids

soluble in organic solvents but not in water

Lipids

an important feature in cell membranes.

Waxes

Ester of a long-chain alcohol and a fatty acid

Lipids containing glycerol

Contain the alcohol glycerol as backbone

Lipids with sphingosines as backvine

Contain a sphingosine backbone

Steroid nucleus

three cyclohexane rings and one cyclopentane ring, fused together.

Steroid nucleus

rings designated as A, B, C, and D.

Steroid nucleus

numbered carbon atoms beginning in ring A.

Steroid nucleus

two methyl groups at positions 18 and 19.

Steroid

contain a fused four-membered ring system

Fatty acids

contain long carbon chains

fatty acids

include carboxyl groups

Fatty acids

Simplest type of lipid

Fatty acids

Long, unbranched carbon chain with a carboxylic acid group at the end

Faty acids

Typically, 12-18 carbons long

Carbon no.1

In delta nomenclature, - is the Carboxyl Carbon

C=C

In omega nomenclature, - position can be denoted by counting from the methyl terminus

Lauric acid

12:0

14:0

Myristic scid

Palmitic acid

16:0

Stearic acid

18:0

Saturated fas

Only C-C bonds are present (single bonds)

Saturated fas

Rich sources of dietary saturated fatty acids include

butter fat

meat fat

and tropical oils (palm oil, coconut oil, and palm kernel oil)

Bad cholesterol

These raise the number of low-density lipoproteins (LDL) or -

High

- -imfa if saturares fas

Monounsaturated fas

Contains one C=C bond (double bond)

Monounsaturated fas

Plant oils (olive, canola, peanut, sesame)

Plant foods (avocados, nuts, seeds)

Animal fats (poultry, lard, beef, dairy, fish)

Dark chocolate

Good cholesterol

Monounsaturated FAs lower LDL and increase high-density lipoproteins (HDL) or - Provided that the monounsaturated FAs are natural (cis)

Polyunsaturated Fas

Has at least two C=C bonds (double bonds)

Linoleic acid w-6

18:2

Linolenic acid w-3

18:3

Arachidonic acid , w-6

20:4

Essential fatty acids

Linoeic 18:2

Linolenic 18:3

Arachidonic acid 20:4

Humans cannot synthesize sufficient amounts of polyunsaturated fatty acids such as

Essential fatty acids

These FAs must be obtained from diet

Omega 3s

Support heart, brain, and vision health

Calms inflammation

Commonly found from fish oils and plant oils

Omega 6s

Promote healthy cell function

Also promotes inflammations

Commonly found in meat, eggs, and vegetable oils

One or more

Almost all naturally occurring unsaturated FAs have - or - cis double bonds

Trans transfats

may increase risk of coronary disease

Cis fas

have been shown to be cardioprotective

Saturated fa

chains pack tightly, leading to high IMFA

Trans fa chains

are almost like saturated FAs but the double bond introduces a kink

Cis fas

have a sharp bend/kink in the chain which severely minimizes IMFA

Higher, higher

-IMFA, -MP

Higher, higher, higher

-#C, -IMFA, -MP

Higher, lower, lower

-double bond, -IMFA,-MP

Fats, trans, saturares

are usually solid at room temperature

usually come from animal sources such as meat, whole milk, butter, and cheese

Oil, unsaturated

are usually liquid at room temperature.

are usually obtained from a plant source such as corn and olive.

Prostaglandingd

Also known as eicosanoids

Prostaglandins

Formed from arachidonic acid (20:4) w-6

Prostaglandins

Hormone-like substances produced in small amounts

Prostaglandins e and f

Differ by attached substituent to the five-carbon ring

Prostaglandins

When tissues are injured, arachidonic acid is converted to -that produce inflammation and pain in the area

NSAISS

Non-steroidal anti-inflammatory drugs

NSAIS

Block production of prostaglandins, decreasing pain and inflammation

Prostaglandins

Promotes fever during infection

Smooth muscle contraction

Vasodilation and blood flow

Blood clotting

Gastroprotection

Kidney function

Waxes

Ester of a long-chain alcohol and a fatty acid

Waxes

Naturally found in plants and animals

Found on the surface of fruits and on leaves and stems, preventing water loss and damage of pests

Found on the skin, fur, and feathers of animals that providing a waterproof coating

Triacylglycerols tags

In the body, fatty acids are stored as

TAGS

are esters of glycerol (a trihydroxy alcohol) and fatty acids.

Tags

are the major form of energy storage for animals.

Tracy glycerols

Animals that hibernate eat large quantities of plants, seeds, and nuts that are high in calories. During hibernation, their stored fat in the form of -

Glyceryl, carboxylates

In naming, glycerol is named - and the fatty acids are named as -

Mixed triacylglyceril

TAGs may contain different fatty acids

Hydrogenation

Double bonds (C=C) are converted into single bonds (C-C)