Carbon atom numbering[edit]

See also: Essential fatty acid §  Nomenclature and terminology

Numbering of carbon atoms. The systematic (IUPAC) C-x numbers are in blue. The omega-minus "ω−x" labels
are in red. The Greek letter labels are in green. [16] Note that unsaturated fatty acids with a cis configuration are
actually "kinked" rather than straight as shown here.

Most naturally occurring fatty acids have an unbranched chain of carbon atoms, with a carboxyl
group (–COOH) at one end, and a methyl group (–CH3) at the other end.
The position of the carbon atoms in the backbone of a fatty acid are usually indicated by counting
from 1 at the −COOH end. Carbon number x is often abbreviated C-x (or sometimes Cx), with x=1,
2, 3, etc. This is the numbering scheme recommended by the IUPAC.
Another convention uses letters of the Greek alphabet in sequence, starting with the first
carbon after the carboxyl. Thus carbon α (alpha) is C-2, carbon β (beta) is C-3, and so forth.
Although fatty acids can be of diverse lengths, in this second convention the last carbon in the chain
is always labelled as ω (omega), which is the last letter in the Greek alphabet. A third numbering
convention counts the carbons from that end, using the labels "ω", "ω−1", "ω−2". Alternatively, the
label "ω−x" is written "n−x", where the "n" is meant to represent the number of carbons in the chain.
[16]

In either numbering scheme, the position of a double bond in a fatty acid chain is always specified by
giving the label of the carbon closest to the carboxyl end.[16] Thus, in an 18 carbon fatty acid, a
double bond between C-12 (or ω−6) and C-13 (or ω−5) is said to be "at" position C-12 or ω−6. The
IUPAC naming of the acid, such as "octadec-12-enoic acid" (or the more pronounceable variant "12-
octadecanoic acid") is always based on the "C" numbering.
The notation Δx,y,... is traditionally used to specify a fatty acid with double bonds at positions x,y,....
(The capital Greek letter "Δ" (delta) corresponds to Roman "D", for Double bond). Thus, for example,
the 20-carbon arachidonic acid is Δ5,8,11,14, meaning that it has double bonds between carbons 5 and
6, 8 and 9, 11 and 12, and 14 and 15.
In the context of human diet and fat metabolism, unsaturated fatty acids are often classified by the
position of the double bond closest to the ω carbon (only), even in the case of multiple double
bonds such as the essential fatty acids. Thus linoleic acid (18 carbons, Δ9,12), γ-linolenic acid (18-
carbon, Δ6,9,12), and arachidonic acid (20-carbon, Δ5,8,11,14) are all classified as "ω−6" fatty acids;
meaning that their formula ends with –CH=CH–CH
2–CH

2–CH

2–CH

2–CH

3.

Fatty acids with an odd number of carbon atoms are called odd-chain fatty acids, whereas the rest
are even-chain fatty acids. The difference is relevant to gluconeogenesis.
Triterpenoids[edit]

Cholesterol: one of the simplest but most important triterpenoids

By definition triterpenoids are triterpenes that possess heteroatoms, usually oxygen. The

terms triterpene and triterpenoid often are used interchangeably.
Triterpenoids possess a rich chemistry and pharmacology (e.g. cholesterol) with several pentacyclic
motifs. Lupane, oleanane and ursane show particular promise as anti-cancer agents.[5][6]

Steroids[edit]
Steroids feature a cucurbitane core, although in practice they are biosynthesised from
either lanosterol (animals and fungi) or cycloartenol (plants) via the cyclization of squalene. Steroids
have two principal biological functions, being either key components of cell membranes or signaling
molecules that activate steroid hormone receptors. Important sub-classes
include sterols and cucurbitacins.

Triterpenoid saponins[edit]
Triterpenoid saponins are triterpenes which belong to the saponin group of compounds, making
them triterpenoid glycosides. They are produced by plants as part of their self-defense
mechanism[7] with important sub-classes including ginsenosides[8] and eleutherosides.