HYDROCARBONS Flashcards
carbon compounds which contain only carbon and hydrogen
hydrocarbons
organic acids
RCOOH
- high frequency on living organisms
- participate in essential metabolism
- function in association with coenzymes
- accumulate as simple salts, ester, and amides
ORGANIC ACIDS
MONOBASIC ACIDS
- intermediates in the early stages of the biosynthesis of fats, isoprenoid compounds and various amino acids
- present in esterified form (plant kingdom)
C1-C6 Monocarboxylic acid
(hydroxy or keto derivatives)
(-OH, ROR)
MONOBASIC ACIDS
C1-C6 Monocarboxylic acids are present in what form
esterified form
MONOBASIC ACIDS
- important component of plant
- common in lipids and related substances
- obtained by hydrolysis of fats
- usually contains even number of carbon atoms
- occur mainly as esters of natural fats and oils but do occur in the unesterified form as free fatty acids
Fatty acids
MONOBASIC ACIDS
two common aromatic acids
benzoic
cinnamic
MONOBASIC ACIDS | C1-C6 MONOCARBOXYLIC ACID
- HCOOH
- Formica rufa (red ant)
- Stinging nettle (Urtica dioica)
- combined in the gitaloxigenin (cardioactive glycosides) and N-formyl-L-methionine
FORMIC ACID
MONOBASIC ACIDS | C1-C6 MONOCARBOXYLIC ACID
- an intermediate metabolite in the form of acetyl CoA
- common in esterified form
ACETIC ACID
MONOBASIC ACIDS | C1-C6 MONOCARBOXYLIC ACID
Formic acid is combined in ____ and ____
gitaloxigenin & N-formyl-L-methionine
cardioactive glycosides
gitaloxigenin
MONOBASIC ACIDS | C1-C6 MONOCARBOXYLIC ACID
Acetic acid is common in what form
esterified form
MONOBASIC ACIDS | C1-C6 MONOCARBOXYLIC ACID
- produced in the fatty acid
- oxidative cycle when an acyl-CoA with an odd number of carbon atoms is involved
PROPIONIC ACID
MONOBASIC ACIDS | C1-C6 MONOCARBOXYLIC ACID
Propionic acid is porduced in the
fatty acid
MONOBASIC ACIDS | C1-C6 MONOCARBOXYLIC ACID
PROPIONIC ACID:
when does oxidative cycle occurs
when an acyl-CoA w/ odd number C atoms is involved
MONOBASIC ACIDS | C1-C6 MONOCARBOXYLIC ACID
- Ceratonia siliqua (Carob beans), Croton oil (ethyl ester)
- resin component of Convolvulaceae and minor tropane alkaloids
ISO-BUTYRIC ACID
MONOBASIC ACIDS | C1-C6 MONOCARBOXYLIC ACID
substitute for chocolates
Carob beans
Ceratonia siliqua
MONOBASIC ACIDS | C1-C6 MONOCARBOXYLIC ACID
Iso-butyric acid is the resin component of ____ & ____
Convolvulaceae
minor tropane alkaloids
MONOBASIC ACIDS | C1-C6 MONOCARBOXYLIC ACID
- combine/free on Valeriana spp., combine (valeroidine) tropane alkaloids, pyranocoumarin, dihyrosamidin
- may induce drowsiness, preterm labor or abortion
VALERIC & ISO-VALERIC ACID
MONOBASIC ACIDS | C1-C6 MONOCARBOXYLIC ACID
VALERIC & ISO-VALERIC ACID:
which is not common?
Valeric
MONOBASIC ACIDS | C1-C6 MONOCARBOXYLIC ACID
Valeric & Iso-valeric acid are found in what plant
Valeriana spp
MONOBASIC ACIDS | C1-C6 MONOCARBOXYLIC ACID
Valeriana spp is available as
tea
MONOBASIC ACIDS | C1-C6 MONOCARBOXYLIC ACID
Valeriana spp. use/s
anxiolytic
MONOBASIC ACIDS | C1-C6 MONOCARBOXYLIC ACID
Contraindication for Valeric & Iso-valeric acid
abortion
not used in pregnant women
MONOBASIC ACIDS | C1-C6 MONOCARBOXYLIC ACID
- present in tropane and Veratrum alkaloids, convolvulaceous glycosides and visnadin (pyranocoumarin)
2-METHYLBUTYRIC ACID
MONOBASIC ACIDS | C1-C6 MONOCARBOXYLIC ACID
- croton oil (Croton tiglium)
- unsaturated
CROTONOIC ACID (trans-butenoic acid)
MONOBASIC ACIDS | C1-C6 MONOCARBOXYLIC ACID
Crotonoic acid is also known as
trans-butenoic acid
MONOBASIC ACIDS | C1-C6 MONOCARBOXYLIC ACID
- glycoside (croton oil), minor acid in tigloidine
- present in Convolvulaceous resins and Symphytum alkaloids
TIGLIC ACID
MONOBASIC ACIDS | C1-C6 MONOCARBOXYLIC ACID
Tiglic acid is minor acid in
tigloidine
MONOBASIC ACIDS | C1-C6 MONOCARBOXYLIC ACID
- present in the rhizome of Angelica, schizanthine, chamomile oil
- component of cevadine and Symphytum alkaloid
ANGELIC ACID
MONOBASIC ACIDS | C1-C6 MONOCARBOXYLIC ACID
occurs in traces in many fats
n-butyric acid & caproic acid
MONOBASIC ACIDS | C1-C6 MONOCARBOXYLIC ACID
- present in Senecio, alkaloids of Dioscorea & Schizanthus
- present in samidin (pyranocoumarin)
SENECIOIC ACID
MONOBASIC ACIDS
fats are obtained from
hydrolysis of fats
MONOBASIC ACIDS
a fatty acid that does not contain an even number of atoms
margaric acid
MONOBASIC ACIDS | FATTY ACIDS
- no double bonds
- stearic, palmitic
saturated
MONOBASIC ACIDS | FATTY ACIDS
- containing one or more double bonds
UNSATURATED
MONOBASIC ACIDS | FATTY ACIDS
NOMENCLATURE:
saturated
-anoic
MONOBASIC ACIDS | FATTY ACIDS
NOMECLATURE;
unsaturated
-enoic
MONOBASIC ACIDS | FATTY ACIDS
terminal methyl C is known as ____ which indicate the number and position of the double bond
omega
MONOBASIC ACIDS | FATTY ACIDS
what makes them reactive
removal of H
MONOBASIC ACIDS | FATTY ACIDS
- source: Soft coral (Plexaura homomalla)
- involved in platelet aggregation and inflammatory process
- promote smooth muscle contraction
- act as bronchospasmodic and in the development of local anesthetics
PGA2
Prostaglandin A2
MONOBASIC ACIDS | AROMATIC ACIDS
occurs in coca leaves
Cinnamic acid
MONOBASIC ACIDS | AROMATIC ACIDS
o-hydroxybenzoic acid
salicylic acid
MONOBASIC ACIDS | AROMATIC ACIDS
3,4-dihydroxybenzoic acid
Protocatechuic acid
MONOBASIC ACIDS | AROMATIC ACIDS
3,4-dimethoxybenzoic acid
Veratric acid
MONOBASIC ACIDS | AROMATIC ACIDS
3,4,5-trihydroxybenzoic acid
Gallic acid
MONOBASIC ACIDS | AROMATIC ACIDS
p-hydroxycinnamic acid
P-coumaric acid
MONOBASIC ACIDS | AROMATIC ACIDS
hydroxymethoxycinnamic acid
Ferulic acid
MONOBASIC ACIDS | AROMATIC ACIDS
hydroxycinnamic acid
Caffeic acid
MONOBASIC ACIDS | AROMATIC ACIDS
tetrahydrozyhexabonzoic acid
quinic acid
MONOBASIC ACIDS | AROMATIC ACIDS
acid with an alcohol group present in Cinchona and in some gymnosperm
Quinic acid
MONOBASIC ACIDS | AROMATIC ACIDS
from genus Prunus (almonds)
Mandelic acids
MONOBASIC ACIDS | AROMATIC ACIDS
- served as important metabolite sources for star anise (chinese), needles of Pinaceae and gum tree Liquidambar styraciflua
Shikimic acid
toxic star anise
japanese
MONOBASIC ACIDS | AROMATIC ACIDS
Caffeotannic acid (condensation product of caffeic + quinic acid)
chlorogenic acid
MONOBASIC ACIDS | AROMATIC ACIDS
what reaction occurs between caffeic & quinic acid to produce caffeotannic acid
condensation
MONOBASIC ACIDS
- preservative of choice for fresh fruit juices
- constituent of Whitfield’s ointment which is used for the treatment of fungal skin diseases such as tinea, ringworm, and athlete’s foot
Benzoic acid & its salt
MONOBASIC ACIDS | BENZOIC ACID & ITS SALT
- sodium salt of benzoic acid
- used preferably as one of the principal antimicrobial preservatives in food and beverages
- also used in medications, anti-fermentation additives and tableting lubricant for phramaceuticals
SODIUM BENZOATE
MONOBASIC ACIDS | BENZOIC ACID & ITS SALT
- keratolytic
- fungicidal
- treatment of hyperkeratotic, dandruff, ichthyosis, and psoriasis
- antiseptic in toothpaste
SALICYLIC ACID
MONOBASIC ACIDS | BENZOIC ACID & ITS SALT
SALICYLIC ACID:
tx of hyperpigmentation and warts
keratolytic
MONOBASIC ACIDS | BENZOIC ACID & ITS SALT
SALICYLIC ACID:
tx of fungal skin infections such as tinea
fungicidal
MONOBASIC ACIDS | DIBASIC ACID
COOH₂
* bleaching agent
Oxalic acid
MONOBASIC ACIDS | DIBASIC ACID
source of oxalic acid
kamias, star fruit
MONOBASIC ACIDS | DIBASIC ACID
CH₂(COOH)₂
MALONIC ACID
MONOBASIC ACIDS | DIBASIC ACID
(CH₂)₂(COOH)₂
SUCCINIC ACID
MONOBASIC ACIDS | DIBASIC ACID
[COOH-CH=CH-COOH]
FUMARIC ACID
MONOBASIC ACIDS | DIBASIC ACID
(COOH-CH₂-CHOH-COOH)
* skin of apple (Malus domestica)
MALIC ACID
MONOBASIC ACIDS | DIBASIC ACID
COOH-(CHOH)2-COOH
* tamarind especially unripe
* brown when ripe due to inverted sugar and laxative potential
TARTARIC ACID
MONOBASIC ACIDS
- Citric acid (acidolant)
- Isocitric acid
- Aconitic acid (Aconitum spp.)
TRIBASIC ACIDS
- -ol; possess one or more hydroxyl groups (free or ester)
- can be classified as: primary, secondary, tertiray
ALCOHOLS
ALCOHOLS
- aliphatic
- esters like methyl salicylate (source: Betula lenta)
- esters of long-chain alcohols: cetyl, ceryl, myricyl, myricyl ceroate
MONOHYDRIC ALCOHOLS
MONOHYDRIC ALCOHOLS
source of methyl salicylate
Betula lenta
MONOHYDRIC ALCOHOLS
- fruity odor
- Oil of Wintergreen / Betula
methyl salicylate
MONOHYDRIC ALCOHOLS
C₁₆H₃₃OH
cetyl alcohol
MONOHYDRIC ALCOHOLS
C₂₆H₅₃OH
CERYL ALCOHOL
MONOHYDRIC ALCOHOLS
C₃₀H₆₁OH
MYRICYL ALCOHOL
MONOHYDRIC ALCOHOLS
- Carnauba wax
- tablet polishing agent
myricyl cerotate
AROMATIC ALCOHOLS
C₆H₅CH₂OH
BENZYL ALCOHOL
AROMATIC ALCOHOLS
C₆H₅CH=CHCH₂OH
CINNAMYL ALCOHOL
AROMATIC ALCOHOLS
- component of the important strengthening compound in the material of plant cell wall (lignin)
- from heartwood
CONIFERYL ALCOHOL
strengthening compound in the plant cell wall
lignin
AROMATIC ALCOHOLS
Coniferyl alcohol is from
heartwood
ALCOHOL
- Benzyl alcohol
- Cinnamyl alcohol
- Coniferyl alcohol
AROMATIC
ALCOHOLS
- from MVA pathway
- noncyclic
- monocyclic
- dicyclic
TERPENE ALCOHOLS
ALCOHOLS
Terpene alcohols are from what pathway
MVA - mevalonic acid
TERPENE ALCOHOLS
- geraniol (otto of rose)
- nerol (orange and bergamot)
- linalol (as linalyl acetate in lavender and rosemary)
noncyclic
TERPENE ALCOHOLS
NONCYCLIC:
otto of rose
geraniol
TERPENE ALCOHOLS
NONCYCLIC:
orange and bergamot
nerol
TERPENE ALCOHOLS
NONCYCLIC:
as linalyl acetate in lavender and rosemary
linalol
TERPENE ALCOHOLS
- terpeneol (neroli oil)
- menthol (peppermint oil)
monocyclic
TERPENE ALCOHOLS
MONOCYCLIC:
neroli oil
terpineol
TERPENE ALCOHOLS
MONOCYCLIC:
peppermint oil
menthol
TERPENE ALCOHOLS
- Sabinol (Juniperus sabina)
- borneol
dicyclic
ALCOHOLS
- aka glycols
- 3,6-dihydroxytropane
- Panaxadiol (component of ginseng steroid)
- Plyenediol or oenanthotoxin (toxic component of hemclock)
DIHYDIC ALCOHOLS
DIHYDRIC ALCOHOLS
component of ginseng steroid
PANAXADIOL
DIHYDRIC ALCOHOLS
toxic component of hemlock
POLYENEDIOL / OENANTHOTOXIN
ALCOHOLS
aka glycerol
TRIHYDRIC ALCOHOLS
ALCOHOLS
- Carbohydrates
- Meso-erythritol
- Hexahydric sugar alcohols
POLYHYDRIC ALIPHATIC ALCOHOL
POLYHYDRIC ALIPHATIC ALCOHOLS
found in seaweeds & lichens
MESO-ERYTHRITOL
POLYHYDRIC ALIPHATIC ALCOHOL
- sorbitol (rosaceous fruits)
- mannitol (manna)
- dulcitol (Euonymus)
all are artifical sweetening agent (non sugar)
HEXAHYDRIC SUGAR ALCOHOLS
POLYHYDRIC ALIPHATIC ALCOHOL | HEXAHYDRIC SUGAR ALCOHOLS
SOURCE:
sorbitol
rosaceous fruits
POLYHYDRIC ALIPHATIC ALCOHOL | HEXAHYDRIC SUGAR ALCOHOLS
SOURCE:
mannitol
manna
POLYHYDRIC ALIPHATIC ALCOHOL | HEXAHYDRIC SUGAR ALCOHOLS
SOURCE:
dulcitol
euonymus
OTHER ALCOHOLS
- 92.3% by weight
- 94.9% or 95% by volume
- 70% used as local anti-infective
ETHANOL
OTHER ALCOHOLS
ETHANOL:
% by weight
92.3%
OTHER ALCOHOLS
ETHANOL:
% by volume
94.9% or 95%
OTHER ALCOHOLS
ETHANOL:
% as local anti-infective
70%
OTHER ALCOHOLS
48.4% - 49.5% used as solvent
DILUTED ALCOHOL
OTHER ALCOHOLS
% of diluted alcohol used as solvent
48.4% - 49.5%
OTHER ALCOHOLS
distillation from wine
BRANDY
OTHER ALCOHOLS
fermented malted grain
WHISKY
OTHER ALCOHOLS
fermented molasses
RUM
- chemical combination of COOH and OH with release of water
- dehydration condensation
ESTERS