Epicuticular Wax
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Epicuticular wax is a coating of
wax Waxes are a diverse class of organic compounds that are lipophilic, malleable solids near ambient temperatures. They include higher alkanes and lipids, typically with melting points above about 40 °C (104 °F), melting to giv ...
covering the outer surface of the
plant cuticle A plant cuticle is a protecting film covering the outermost skin layer (epidermis) of leaves, young shoots and other aerial plant organs (aerial here meaning all plant parts not embedded in soil or other substrate) that have no ''periderm''. The ...
in
land plants The Embryophyta (), or land plants, are the most familiar group of green plants that comprise vegetation on Earth. Embryophytes () have a common ancestor with green algae, having emerged within the Phragmoplastophyta clade of green algae as sist ...
. It may form a whitish film or bloom on leaves, fruits and other plant organs. Chemically, it consists of hydrophobic organic compounds, mainly straight-chain
aliphatic In organic chemistry, hydrocarbons ( compounds composed solely of carbon and hydrogen) are divided into two classes: aromatic compounds and aliphatic compounds (; G. ''aleiphar'', fat, oil). Aliphatic compounds can be saturated, like hexane, ...
hydrocarbon In organic chemistry, a hydrocarbon is an organic compound consisting entirely of hydrogen and carbon. Hydrocarbons are examples of group 14 hydrides. Hydrocarbons are generally colourless and hydrophobic, and their odors are usually weak or ex ...
s with or without a variety of substituted
functional group In organic chemistry, a functional group is a substituent or moiety in a molecule that causes the molecule's characteristic chemical reactions. The same functional group will undergo the same or similar chemical reactions regardless of the rest ...
s. The main functions of the epicuticular wax are to decrease surface wetting and moisture loss. Other functions include reflection of ultraviolet light, assisting in the formation of an ultra-hydrophobic and self-cleaning surface and acting as an anti-climb surface.


Chemical composition

Common constituents of epicuticular wax are predominantly straight-chain
aliphatic In organic chemistry, hydrocarbons ( compounds composed solely of carbon and hydrogen) are divided into two classes: aromatic compounds and aliphatic compounds (; G. ''aleiphar'', fat, oil). Aliphatic compounds can be saturated, like hexane, ...
hydrocarbon In organic chemistry, a hydrocarbon is an organic compound consisting entirely of hydrogen and carbon. Hydrocarbons are examples of group 14 hydrides. Hydrocarbons are generally colourless and hydrophobic, and their odors are usually weak or ex ...
s that may be saturated or unsaturated and contain a variety of functional groups. These waxes can be composed of a variety of compounds which differ between plant species. Paraffins occur in leaves of
pea The pea is most commonly the small spherical seed or the seed-pod of the flowering plant species ''Pisum sativum''. Each pod contains several peas, which can be green or yellow. Botanically, pea pods are fruit, since they contain seeds and d ...
s and
cabbage Cabbage, comprising several cultivars of ''Brassica oleracea'', is a leafy green, red (purple), or white (pale green) biennial plant grown as an annual vegetable crop for its dense-leaved heads. It is descended from the wild cabbage ( ''B.&nb ...
s. Leaves of
carnauba Carnauba (; pt, carnaúba ), also called Brazil wax and palm wax, is a wax of the leaves of the carnauba palm ''Copernicia prunifera'' (synonym: ''Copernicia cerifera''), a plant native to and grown only in the northeastern Brazilian states of ...
palm and
banana A banana is an elongated, edible fruit – botanically a berry – produced by several kinds of large herbaceous flowering plants in the genus ''Musa''. In some countries, bananas used for cooking may be called "plantains", distinguis ...
feature alkyl
ester In chemistry, an ester is a compound derived from an oxoacid (organic or inorganic) in which at least one hydroxyl group () is replaced by an alkoxy group (), as in the substitution reaction of a carboxylic acid and an alcohol. Glycerides ar ...
s. The
secondary alcohol In chemistry, an alcohol is a type of organic compound that carries at least one hydroxyl () functional group bound to a saturated carbon atom. The term ''alcohol'' originally referred to the primary alcohol ethanol (ethyl alcohol), which is ...
10-nonacosanol appears in most
gymnosperms The gymnosperms ( lit. revealed seeds) are a group of seed-producing plants that includes conifers, cycads, ''Ginkgo'', and gnetophytes, forming the clade Gymnospermae. The term ''gymnosperm'' comes from the composite word in el, γυμνό ...
such as ''
Ginkgo biloba ''Ginkgo biloba'', commonly known as ginkgo or gingko ( ), also known as the maidenhair tree, is a species of tree native to China. It is the last living species in the order Ginkgoales, which first appeared over 290 million years ago. Fossils ...
'' and Sitka spruce as well as many of the
Ranunculaceae Ranunculaceae (buttercup or crowfoot family; Latin "little frog", from "frog") is a family of over 2,000 known species of flowering plants in 43 genera, distributed worldwide. The largest genera are ''Ranunculus'' (600 species), ''Delphinium' ...
,
Papaveraceae The Papaveraceae are an economically important family of about 42 genera and approximately 775 known species of flowering plants in the order Ranunculales, informally known as the poppy family. The family is cosmopolitan, occurring in temperat ...
and
Rosaceae Rosaceae (), the rose family, is a medium-sized family of flowering plants that includes 4,828 known species in 91 genera. The name is derived from the type genus ''Rosa''. Among the most species-rich genera are ''Alchemilla'' (270), ''Sorbus ...
and some mosses. Other forms of secondary alcohols are found in
Brassicaceae Brassicaceae () or (the older) Cruciferae () is a medium-sized and economically important family of flowering plants commonly known as the mustards, the crucifers, or the cabbage family. Most are herbaceous plants, while some are shrubs. The le ...
including ''
Arabidopsis thaliana ''Arabidopsis thaliana'', the thale cress, mouse-ear cress or arabidopsis, is a small flowering plant native to Eurasia and Africa. ''A. thaliana'' is considered a weed; it is found along the shoulders of roads and in disturbed land. A winter a ...
.''
Primary alcohol A primary alcohol is an alcohol in which the hydroxy group is bonded to a primary carbon atom. It can also be defined as a molecule containing a “–CH2OH” group. In contrast, a secondary alcohol has a formula “–CHROH” and a tertiary ...
s (most commonly
octacosan-1-ol 1-Octacosanol (also known as ''n''-octacosanol, octacosyl alcohol, cluytyl alcohol, montanyl alcohol) is a straight-chain aliphatic 28-carbon primary fatty alcohol that is common in the epicuticular waxes of plants, including the leaves of many ...
) occur in ''
Eucalyptus ''Eucalyptus'' () is a genus of over seven hundred species of flowering trees, shrubs or mallees in the myrtle family, Myrtaceae. Along with several other genera in the tribe Eucalypteae, including '' Corymbia'', they are commonly known as euca ...
,''
legume A legume () is a plant in the family Fabaceae (or Leguminosae), or the fruit or seed of such a plant. When used as a dry grain, the seed is also called a pulse. Legumes are grown agriculturally, primarily for human consumption, for livestock f ...
s, and most
Poaceae Poaceae () or Gramineae () is a large and nearly ubiquitous family of monocotyledonous flowering plants commonly known as grasses. It includes the cereal grasses, bamboos and the grasses of natural grassland and species cultivated in lawns an ...
grasses. Other grasses feature β-
diketone In organic chemistry, a dicarbonyl is a molecule containing two carbonyl () groups. Although this term could refer to any organic compound containing two carbonyl groups, it is used more specifically to describe molecules in which both carbonyls ...
s, as do ''
Eucalyptus ''Eucalyptus'' () is a genus of over seven hundred species of flowering trees, shrubs or mallees in the myrtle family, Myrtaceae. Along with several other genera in the tribe Eucalypteae, including '' Corymbia'', they are commonly known as euca ...
'', box ''
Buxus ''Buxus'' is a genus of about seventy species in the family Buxaceae. Common names include box or boxwood. The boxes are native to western and southern Europe, southwest, southern and eastern Asia, Africa, Madagascar, northernmost South ...
'' and the
Ericaceae The Ericaceae are a family of flowering plants, commonly known as the heath or heather family, found most commonly in acidic and infertile growing conditions. The family is large, with c.4250 known species spread across 124 genera, making it th ...
. Young
beech Beech (''Fagus'') is a genus of deciduous trees in the family Fagaceae, native to temperate Europe, Asia, and North America. Recent classifications recognize 10 to 13 species in two distinct subgenera, ''Engleriana'' and ''Fagus''. The ''Engle ...
leaves,
sugarcane Sugarcane or sugar cane is a species of (often hybrid) tall, Perennial plant, perennial grass (in the genus ''Saccharum'', tribe Andropogoneae) that is used for sugar Sugar industry, production. The plants are 2–6 m (6–20 ft) tall with ...
culms and
lemon The lemon (''Citrus limon'') is a species of small evergreen trees in the flowering plant family Rutaceae, native to Asia, primarily Northeast India (Assam), Northern Myanmar or China. The tree's ellipsoidal yellow fruit is used for culin ...
fruit exhibit
aldehyde In organic chemistry, an aldehyde () is an organic compound containing a functional group with the structure . The functional group itself (without the "R" side chain) can be referred to as an aldehyde but can also be classified as a formyl grou ...
s.
Triterpene Triterpenes are a class of chemical compounds composed of three terpene units with the molecular formula C30H48; they may also be thought of as consisting of six isoprene units. Animals, plants and fungi all produce triterpenes, including squa ...
s are the primary component in fruit waxes of
apple An apple is an edible fruit produced by an apple tree (''Malus domestica''). Apple fruit tree, trees are agriculture, cultivated worldwide and are the most widely grown species in the genus ''Malus''. The tree originated in Central Asia, wh ...
,
plum A plum is a fruit of some species in ''Prunus'' subg. ''Prunus'.'' Dried plums are called prunes. History Plums may have been one of the first fruits domesticated by humans. Three of the most abundantly cultivated species are not found i ...
and
grape A grape is a fruit, botanically a berry, of the deciduous woody vines of the flowering plant genus ''Vitis''. Grapes are a non- climacteric type of fruit, generally occurring in clusters. The cultivation of grapes began perhaps 8,000 years ago, ...
. Cyclic constituents are often recorded in epicuticular waxes but are generally minor constituents. They may include
phytosterol Phytosterols are phytosteroids, similar to cholesterol, that serve as structural components of biological membranes of plants. They encompass plant sterols and stanols. More than 250 sterols and related compounds have been identified. Free phyto ...
s such as
β-sitosterol β-sitosterol (beta-sitosterol) is one of several phytosterols (plant sterols) with chemical structures similar to that of cholesterol. It is a white, waxy powder with a characteristic odor, and is one of the components of the food additive E499 ...
and pentacyclic
triterpenoids Triterpenes are a class of chemical compounds composed of three terpene units with the molecular formula C30H48; they may also be thought of as consisting of six isoprene units. Animals, plants and fungi all produce triterpenes, including squale ...
such as
ursolic acid Ursolic acid (sometimes referred to as urson, prunol, malol, or 3β-hydroxyurs-12-en-28-oic acid), is a pentacyclic triterpenoid identified in the epicuticular waxes of apples as early as 1920 and widely found in the peels of fruits, as well ...
and
oleanolic acid Oleanolic acid or oleanic acid is a naturally occurring pentacyclic triterpenoid related to betulinic acid. It is widely distributed in food and plants where it exists as a free acid or as an aglycone of triterpenoid saponins. Natural occurren ...
and their respective precursors,
α-amyrin The amyrins are three closely related natural chemical compounds of the triterpene class. They are designated α-amyrin (ursane skeleton), β-amyrin (oleanane skeleton) and δ-amyrin. Each is a pentacyclic triterpenol with the chemical formula C ...
and β-amyrin.


Farina

Many species of the genus ''
Primula ''Primula'' () is a genus of herbaceous flowering plants in the family Primulaceae. They include the primrose ('' P. vulgaris''), a familiar wildflower of banks and verges. Other common species are '' P. auricula'' (auricula), '' P. veris'' (cow ...
'' and ferns such as '' Cheilanthes'', ''
Pityrogramma ''Pityrogramma'', the silverback ferns, or goldback ferns, is a fern genus in the subfamily Pteridoideae of the family Pteridaceae Pteridaceae is a family of ferns in the order Polypodiales, including some 1150 known species in ca 45 genera ...
'' and ''
Notholaena ''Notholaena'' (from Ancient Greek νόθο(ς) + χλαῖνα), cloak fern, is a genus of ferns in the Cheilanthoideae subfamily of the Pteridaceae. Ferns of this genus are mostly epipetric (growing on rock) or occurring in coarse, gravelly soi ...
'' produce a mealy, whitish to pale yellow glandular secretion known as farina that is not an epicuticular wax, but consists largely of crystals of a different class of
polyphenol Polyphenols () are a large family of naturally occurring organic compounds characterized by multiples of phenol units. They are abundant in plants and structurally diverse. Polyphenols include flavonoids, tannic acid, and ellagitannin, some of ...
ic compounds known as
flavonoids Flavonoids (or bioflavonoids; from the Latin word ''flavus'', meaning yellow, their color in nature) are a class of polyphenolic secondary metabolites found in plants, and thus commonly consumed in the diets of humans. Chemically, flavonoids ...
. Unlike epicuticular wax, farina is secreted by specialised glandular hairs, rather than by the cuticle of the entire epidermis.


Physical properties

Epicuticular waxes are mostly solids at ambient temperature, with melting points above about . They are soluble in organic solvents such as
chloroform Chloroform, or trichloromethane, is an organic compound with chemical formula, formula Carbon, CHydrogen, HChlorine, Cl3 and a common organic solvent. It is a colorless, strong-smelling, dense liquid produced on a large scale as a precursor to ...
and
hexane Hexane () is an organic compound, a straight-chain alkane with six carbon atoms and has the molecular formula C6H14. It is a colorless liquid, odorless when pure, and with boiling points approximately . It is widely used as a cheap, relatively ...
, making them accessible for chemical analysis, but in some species esterification of acids and alcohols into estolides or the polymerization of aldehydes may give rise to insoluble compounds. Solvent extracts of cuticle waxes contain both epicuticular and cuticular waxes, often contaminated with
cell membrane The cell membrane (also known as the plasma membrane (PM) or cytoplasmic membrane, and historically referred to as the plasmalemma) is a biological membrane that separates and protects the interior of all cells from the outside environment ( ...
lipids of underlying cells. Epicuticular wax can now also be isolated by mechanical methods that distinguish the epicuticular wax outside the
plant cuticle A plant cuticle is a protecting film covering the outermost skin layer (epidermis) of leaves, young shoots and other aerial plant organs (aerial here meaning all plant parts not embedded in soil or other substrate) that have no ''periderm''. The ...
from the
cuticular wax A cuticle (), or cuticula, is any of a variety of tough but flexible, non-mineral outer coverings of an organism, or parts of an organism, that provide protection. Various types of "cuticle" are non-homology (biology), homologous, differing in th ...
embedded in the cuticle polymer. As a consequence, these two are now known to be chemically distinct, although the mechanism that segregates the molecular species into the two layers is unknown. Recent scanning electron microscopy (SEM),
atomic force microscopy Atomic force microscopy (AFM) or scanning force microscopy (SFM) is a very-high-resolution type of scanning probe microscopy (SPM), with demonstrated resolution on the order of fractions of a nanometer, more than 1000 times better than the op ...
(AFM) and
neutron reflectometry Neutron reflectometry is a neutron diffraction technique for measuring the structure of thin films, similar to the often complementary techniques of X-ray reflectivity and ellipsometry. The technique provides valuable information over a wide var ...
studies on reconstituted wax films have found wheat epicuticular waxes; made up of surface epicuticular crystals and an underlying, porous background film layer to undergo swelling when in contact with water, indicating the background film is permeable and susceptible to the transport of water. Epicuticular wax can reflect UV light, such as the white, chalky, wax coating of ''
Dudleya brittonii ''Dudleya brittonii'', with the common names Britton's dudleya, Britton's liveforever and giant chalk dudleya, is a succulent plant in the family Crassulaceae. It is native to the coast of northern Baja California, Mexico. Both forms of the plan ...
'', which has the highest
ultraviolet light Ultraviolet (UV) is a form of electromagnetic radiation with wavelength from 10 nm (with a corresponding frequency around 30  PHz) to 400 nm (750  THz), shorter than that of visible light, but longer than X-rays. UV radiation i ...
(UV)
reflectivity The reflectance of the surface of a material is its effectiveness in Reflection (physics), reflecting radiant energy. It is the fraction of incident electromagnetic power that is reflected at the boundary. Reflectance is a component of the respon ...
of any known naturally occurring biological substance. The term 'glaucous' is used to refer to any foliage, such as that of the family
Crassulaceae The Crassulaceae (from Latin ''crassus'', thick), also known as the stonecrop family or the orpine family, are a diverse family of dicotyledon flowering plants characterized by succulent leaves and a unique form of photosynthesis, known as Crass ...
, which appears whitish because of the waxy covering. Coatings of epicuticular flavonoids may be referred to as 'farina', the plants themselves being described as 'farinose' or '
farinaceous Flour is a powder made by grinding raw grains, roots, beans, nuts, or seeds. Flours are used to make many different foods. Cereal flour, particularly wheat flour, is the main ingredient of bread, which is a staple food for many culture ...
'.


Epicuticular wax crystals

Epicuticular wax forms crystalline projections from the plant surface, which enhance their water repellency, create a self-cleaning property known as the
lotus effect The lotus effect refers to self-cleaning properties that are a result of ultrahydrophobicity as exhibited by the leaves of ''Nelumbo'', the lotus flower. Dirt particles are picked up by water droplets due to the micro- and nanoscopic architec ...
and reflect UV radiation. The shapes of the crystals are dependent on the wax compounds present in them. Asymmetrical
secondary alcohol In chemistry, an alcohol is a type of organic compound that carries at least one hydroxyl () functional group bound to a saturated carbon atom. The term ''alcohol'' originally referred to the primary alcohol ethanol (ethyl alcohol), which is ...
s and β-diketones form hollow wax
nanotubes file:Chiraltube.png, A scanning tunneling microscopy image of a single-walled carbon nanotube file:Kohlenstoffnanoroehre Animation.gif, Rotating single-walled zigzag carbon nanotube A carbon nanotube (CNT) is a tube made of carbon with diameters ...
, while
primary alcohol A primary alcohol is an alcohol in which the hydroxy group is bonded to a primary carbon atom. It can also be defined as a molecule containing a “–CH2OH” group. In contrast, a secondary alcohol has a formula “–CHROH” and a tertiary ...
s and symmetrical
secondary alcohol In chemistry, an alcohol is a type of organic compound that carries at least one hydroxyl () functional group bound to a saturated carbon atom. The term ''alcohol'' originally referred to the primary alcohol ethanol (ethyl alcohol), which is ...
s form flat plates Although these have been observed using the
transmission electron microscope Transmission electron microscopy (TEM) is a microscopy technique in which a beam of electrons is transmitted through a specimen to form an image. The specimen is most often an ultrathin section less than 100 nm thick or a suspension on a gr ...
and scanning electron microscope the process of growth of the crystals had never been observed directly until Koch and coworkers studied growing wax crystals on leaves of
snowdrop ''Galanthus'' (from Ancient Greek , (, "milk") + (, "flower")), or snowdrop, is a small genus of approximately 20 species of bulbous perennial herbaceous plants in the family Amaryllidaceae. The plants have two linear leaves and a single sm ...
(''
Galanthus ''Galanthus'' (from Ancient Greek , (, "milk") + (, "flower")), or snowdrop, is a small genus of approximately 20 species of bulbous perennial herbaceous plants in the family Amaryllidaceae. The plants have two linear leaves and a single ...
nivalis'') and other species using the
atomic force microscope Atomic force microscopy (AFM) or scanning force microscopy (SFM) is a very-high-resolution type of scanning probe microscopy (SPM), with demonstrated resolution on the order of fractions of a nanometer, more than 1000 times better than the diffr ...
. These studies show that the crystals grow by extension from their tips, raising interesting questions about the mechanism of transport of the molecules.


See also

*
Wax Waxes are a diverse class of organic compounds that are lipophilic, malleable solids near ambient temperatures. They include higher alkanes and lipids, typically with melting points above about 40 °C (104 °F), melting to giv ...
*
Plant cuticle A plant cuticle is a protecting film covering the outermost skin layer (epidermis) of leaves, young shoots and other aerial plant organs (aerial here meaning all plant parts not embedded in soil or other substrate) that have no ''periderm''. The ...
*
Glaucous ''Glaucous'' (, ) is used to describe the pale grey or bluish-green appearance of the surfaces of some plants, as well as in the names of birds, such as the glaucous gull (''Larus hyperboreus''), glaucous-winged gull (''Larus glaucescens''), g ...


References


Bibliography

* {{DEFAULTSORT:Epicuticular Wax Plant anatomy Plant physiology