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Lanolin (from
Latin Latin ( or ) is a classical language belonging to the Italic languages, Italic branch of the Indo-European languages. Latin was originally spoken by the Latins (Italic tribe), Latins in Latium (now known as Lazio), the lower Tiber area aroun ...
'wool', and 'oil'), also called wool fat, wool yolk, wool wax, sheep grease, sheep yolk, or wool grease, is a wax secreted by the
sebaceous gland A sebaceous gland or oil gland is a microscopic exocrine gland in the skin that opens into a hair follicle to secrete an oily or waxy matter, called sebum, which lubricates the hair and skin of mammals. In humans, sebaceous glands occur in ...
s of
wool Wool is the textile fiber obtained from sheep and other mammals, especially goats, rabbits, and camelids. The term may also refer to inorganic materials, such as mineral wool and glass wool, that have some properties similar to animal w ...
-bearing animals. Lanolin used by humans comes from
domestic sheep Sheep (: sheep) or domestic sheep (''Ovis aries'') are a domesticated, ruminant mammal typically kept as livestock. Although the term ''sheep'' can apply to other species in the genus '' Ovis'', in everyday usage it almost always refers to ...
breeds A breed is a specific group of breedable domestic animals having homogeneous appearance (phenotype), homogeneous behavior, and/or other characteristics that distinguish it from other organisms of the same species. In literature, there exist seve ...
that are raised specifically for their wool. Historically, many
pharmacopoeia A pharmacopoeia, pharmacopeia, or pharmacopoea (or the typographically obsolete rendering, ''pharmacopœia''), meaning "drug-making", in its modern technical sense, is a reference work containing directions for the identification of compound med ...
s have referred to lanolin as wool fat ('' adeps lanae''); however, as lanolin lacks
glycerides Glycerides, also known as acylglycerols, are esters formed from glycerol and fatty acids, and are generally very hydrophobic. Glycerol has three hydroxyl functional groups, which can be esterified with one, two, or three fatty acids to form mo ...
(glycerol esters), it is not a true fat. Lanolin primarily consists of
sterol A sterol is any organic compound with a Skeletal formula, skeleton closely related to Cholestanol, cholestan-3-ol. The simplest sterol is gonan-3-ol, which has a formula of , and is derived from that of gonane by replacement of a hydrogen atom on ...
esters instead. Lanolin's
waterproofing Waterproofing is the process of making an object, person or structure waterproof or water-resistant so that it remains relatively unaffected by water or resists the ingress of water under specified conditions. Such items may be used in wet env ...
property aids sheep in shedding water from their coats. Certain breeds of sheep produce large amounts of lanolin. Lanolin's role in nature is to protect wool and skin from climate and the environment; it also plays a role in skin ( integumental) hygiene. Lanolin and its derivatives are used in the protection, treatment, and beautification of human skin.


Composition

A typical high-purity grade of lanolin is composed predominantly of long chain waxy
ester In chemistry, an ester is a compound derived from an acid (either organic or inorganic) in which the hydrogen atom (H) of at least one acidic hydroxyl group () of that acid is replaced by an organyl group (R). These compounds contain a distin ...
s (approximately 97% by weight) with the remainder being lanolin
alcohol Alcohol may refer to: Common uses * Alcohol (chemistry), a class of compounds * Ethanol, one of several alcohols, commonly known as alcohol in everyday life ** Alcohol (drug), intoxicant found in alcoholic beverages ** Alcoholic beverage, an alco ...
s, lanolin
acid An acid is a molecule or ion capable of either donating a proton (i.e. Hydron, hydrogen cation, H+), known as a Brønsted–Lowry acid–base theory, Brønsted–Lowry acid, or forming a covalent bond with an electron pair, known as a Lewis ...
s and lanolin
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 Hydrophobe, hydrophobic; their odor is usually fain ...
s. An estimated 8,000 to 20,000 different types of lanolin esters are present in lanolin, resulting from combinations between the 200 or so different lanolin acids and the 100 or so different lanolin alcohols identified so far. Lanolin’s complex composition of long-chain esters, hydroxyesters, diesters, lanolin alcohols, and lanolin acids means in addition to its being a valuable product in its own right, it is also the starting point for the production of a whole spectrum of lanolin derivatives, which possess wide-ranging chemical and physical properties. The main derivatisation routes include
hydrolysis Hydrolysis (; ) is any chemical reaction in which a molecule of water breaks one or more chemical bonds. The term is used broadly for substitution reaction, substitution, elimination reaction, elimination, and solvation reactions in which water ...
, fractional solvent
crystallisation Crystallization is a process that leads to solids with highly organized atoms or molecules, i.e. a crystal. The ordered nature of a crystalline solid can be contrasted with amorphous solids in which atoms or molecules lack regular organization ...
,
esterification In chemistry, an ester is a compound derived from an acid (either organic or inorganic) in which the hydrogen atom (H) of at least one acidic hydroxyl group () of that acid is replaced by an organyl group (R). These compounds contain a distin ...
,
hydrogenation Hydrogenation is a chemical reaction between molecular hydrogen (H2) and another compound or element, usually in the presence of a catalyst such as nickel, palladium or platinum. The process is commonly employed to redox, reduce or Saturated ...
,
alkoxylation Alkoxylation is a chemical reaction that involves the addition of an epoxide to another compound. The usual manifestation of this reaction is ethoxylation of alcohols (ROH), in which case ethylene oxide is the alkoxylating agent: :ROH + C2H4O ...
and quaternisation. Lanolin derivatives obtained from these processes are used widely in both high-value cosmetics and skin treatment products.
Hydrolysis Hydrolysis (; ) is any chemical reaction in which a molecule of water breaks one or more chemical bonds. The term is used broadly for substitution reaction, substitution, elimination reaction, elimination, and solvation reactions in which water ...
of lanolin yields lanolin alcohols and lanolin acids. Lanolin alcohols are a rich source of
cholesterol Cholesterol is the principal sterol of all higher animals, distributed in body Tissue (biology), tissues, especially the brain and spinal cord, and in Animal fat, animal fats and oils. Cholesterol is biosynthesis, biosynthesized by all anima ...
(an important skin lipid) and are powerful water-in-oil
emulsifier An emulsion is a mixture of two or more liquids that are normally immiscible (unmixable or unblendable) owing to liquid-liquid phase separation. Emulsions are part of a more general class of two-phase systems of matter called colloids. Althou ...
s; they have been used extensively in skincare products for over 100 years. Approximately 40% of the acids derived from lanolin are
alpha-hydroxy acid Alpha hydroxy carboxylic acids, or α-hydroxy carboxylic acids (AHAs), are a group of carboxylic acids featuring a hydroxy group located ''one'' carbon atom away from the acid group. This structural aspect distinguishes them from beta hydroxy aci ...
s (AHAs). The use of AHAs in skin care products has attracted a great deal of attention in recent years. Details of the AHAs isolated from lanolin can be seen in the table below.


Production

Crude lanolin constitutes about 5–25% of the weight of freshly shorn wool. The wool from one
Merino sheep The Merino is a list of sheep breeds, breed or group of breeds of domestic sheep, characterised by very fine soft wool. It was established in Spain near the end of the Middle Ages, and was for several centuries kept as a strict Spanish monop ...
will produce about 250–300 ml of recoverable wool grease. Lanolin is extracted by washing the wool in hot water with a special wool scouring detergent to remove dirt, wool grease (crude lanolin), suint (sweat salts), and anything else stuck to the wool. The wool grease is continuously removed during this washing process by
centrifuge A centrifuge is a device that uses centrifugal force to subject a specimen to a specified constant force - for example, to separate various components of a fluid. This is achieved by spinning the fluid at high speed within a container, thereby ...
separators, which concentrate it into a waxlike substance melting at approximately .


Applications

Lanolin ointment Lanolin and its many derivatives are used extensively in both the personal care (e.g., high value cosmetics, facial cosmetics, lip products) and health care sectors such as topical liniments. Lanolin is also found in lubricants, rust-preventive coatings, shoe polish, and other commercial products. Lanolin is a relatively common allergen and is often misunderstood as a wool allergy. However, allergy to a lanolin-containing product is difficult to pinpoint and often other products containing lanolin may be fine for use. Patch testing can be done if a lanolin allergy is suspected. It is frequently used in protective baby skin treatment and for sore nipples from breastfeeding but health authorities recommend alternative methods first, including nipple cleaning and improving baby positioning as well as expressing milk by hand. Lanolin is reported to have soothing properties but the lack of research leads to the previous recommendations being primary. Lanolin is used commercially in many industrial products ranging from
rust Rust is an iron oxide, a usually reddish-brown oxide formed by the reaction of iron and oxygen in the catalytic presence of water or air moisture. Rust consists of hydrous iron(III) oxides (Fe2O3·nH2O) and iron(III) oxide-hydroxide (FeO(OH) ...
proof coatings to
lubricant A lubricant (sometimes shortened to lube) is a substance that helps to reduce friction between surfaces in mutual contact, which ultimately reduces the heat generated when the surfaces move. It may also have the function of transmitting forces, ...
s. Some sailors use lanolin to create slippery surfaces on their
propeller A propeller (often called a screw if on a ship or an airscrew if on an aircraft) is a device with a rotating hub and radiating blades that are set at a pitch to form a helical spiral which, when rotated, exerts linear thrust upon a working flu ...
s and stern gear to which
barnacles Barnacles are arthropods of the subclass Cirripedia in the subphylum Crustacea. They are related to crabs and lobsters, with similar nauplius larvae. Barnacles are exclusively marine invertebrates; many species live in shallow and tidal water ...
cannot adhere. Commercial products (e.g. Lanocote) containing up to 85% lanolin are used to prevent corrosion in marine fasteners, especially when two different metals are in contact with each other and saltwater. The water-repellent properties make it valuable in many applications as a lubricant grease where
corrosion Corrosion is a natural process that converts a refined metal into a more chemically stable oxide. It is the gradual deterioration of materials (usually a metal) by chemical or electrochemical reaction with their environment. Corrosion engine ...
would otherwise be a problem. 7-Dehydrocholesterol from lanolin is used as a raw material for producing vitamin D3 by irradiation with ultraviolet light.
Baseball player Baseball is a bat-and-ball games, bat-and-ball sport played between two team sport, teams of nine players each, taking turns batting (baseball), batting and Fielding (baseball), fielding. The game occurs over the course of several Pitch ...
s often use it to soften and break in their
baseball glove A baseball glove or mitt is a large glove worn by baseball players of the defending team, which assists players in catching and fielding balls hit by a Batter (baseball), batter or thrown by a teammate. Gloves are traditionally made of leather; b ...
s (
shaving cream Shaving cream or shave cream is a category of cream cosmetics used for shaving preparation. The purpose of shaving cream is to soften the hair by providing lubrication. Different types of shaving creams include aerosol shaving cream (also kn ...
with lanolin is popularly used for this). Anhydrous liquid lanolin, combined with
paraben Parabens are organic compounds that are commonly used as preservatives in cosmetic and pharmaceutical products. They are esters of parahydroxybenzoic acid (also known as 4-hydroxybenzoic acid). Chemistry Structure and structure Parabens a ...
s, has been used in trials as
artificial tears Artificial tears are lubricating eye drops used to relieve dryness and irritation of the ocular surface. Dry eye syndrome ( keratoconjunctivitis sicca) is a common ocular surface disorder and is characterized by disruption of the tear film and ...
to treat
dry eye Dry eye syndrome, also known as keratoconjunctivitis sicca, is the condition of having dry eyes. Symptoms include dryness in the eye, irritation, redness, discharge, blurred vision, and easily fatigued eyes. Symptoms range from mild and occas ...
. Anhydrous lanolin is also used as a lubricant for
brass instrument A brass instrument is a musical instrument that produces sound by Sympathetic resonance, sympathetic vibration of air in a tubular resonator in sympathy with the vibration of the player's lips. The term ''labrosone'', from Latin elements meani ...
tuning slides. Lanolin can also be restored to
wool Wool is the textile fiber obtained from sheep and other mammals, especially goats, rabbits, and camelids. The term may also refer to inorganic materials, such as mineral wool and glass wool, that have some properties similar to animal w ...
len garments to make them water and dirt repellent, such as for cloth diaper covers. Lanolin is also used in
lip balm Lip balm or lip salve is a wax-like substance applied to the lips to moisturize and relieve chapped or dry lips, angular cheilitis, stomatitis, or cold sores. Lip balm often contains beeswax or carnauba wax, camphor, cetyl alcohol, lanolin, par ...
products such as Carmex. For some people, it can irritate the lips. Lanolin is sometimes used by people on
continuous positive airway pressure Continuous positive airway pressure (CPAP) is a form of positive airway pressure (PAP) ventilation in which a constant level of pressure greater than atmospheric pressure is continuously applied to the upper respiratory tract of a person. The a ...
therapy to reduce irritation with masks, particularly nasal pillow masks that can often create sore spots in the
nostril A nostril (or naris , : nares ) is either of the two orifices of the nose. They enable the entry and exit of air and other gasses through the nasal cavities. In birds and mammals, they contain branched bones or cartilages called turbinates ...
s. Lanolin is a popular additive to moustache wax, particularly 'extra-firm' varieties. Lanolin is used as a primary lubricating component in aerosol-based brass
lubricant A lubricant (sometimes shortened to lube) is a substance that helps to reduce friction between surfaces in mutual contact, which ultimately reduces the heat generated when the surfaces move. It may also have the function of transmitting forces, ...
s in the ammunition reloading process. Mixed warm 1:12 with highly concentrated
ethanol Ethanol (also called ethyl alcohol, grain alcohol, drinking alcohol, or simply alcohol) is an organic compound with the chemical formula . It is an Alcohol (chemistry), alcohol, with its formula also written as , or EtOH, where Et is the ps ...
(usually 99%), the ethanol acts as a carrier which evaporates quickly after application, leaving a fine film of lanolin behind to prevent brass seizing in resizing dies. Lanolin, when mixed with ingredients such as
neatsfoot oil Neatsfoot oil is a yellow oil rendered and purified from the shin bones and feet (but not the hooves) of cattle. "Neat" in the oil's name comes from an Old English word for cattle. Neatsfoot oil is used as a conditioning, softening and prese ...
,
beeswax Bee hive wax complex Beeswax (also known as cera alba) is a natural wax produced by honey bees of the genus ''Apis''. The wax is formed into scales by eight wax-producing glands in the abdominal segments of worker bees, which discard it in o ...
and glycerol, is used in various
leather Leather is a strong, flexible and durable material obtained from the tanning (leather), tanning, or chemical treatment, of animal skins and hides to prevent decay. The most common leathers come from cattle, sheep, goats, equine animals, buffal ...
treatments, for example in some
saddle soap Saddle soap is a compound used for cleaning, conditioning, and protecting leather. It typically contains mild soap, softening ingredients such as lanolin, and preservatives such as beeswax. It is commonly used on leather footwear, saddles, and ...
s and in leather care products.


Standards and legislation

In addition to general purity requirements, lanolin must meet official requirements for the permissible levels of
pesticide Pesticides are substances that are used to control pests. They include herbicides, insecticides, nematicides, fungicides, and many others (see table). The most common of these are herbicides, which account for approximately 50% of all p ...
residues. The Fifth Supplement of the
United States Pharmacopoeia The ''United States Pharmacopeia'' (''USP'') is a pharmacopeia (compendium of drug information) for the United States published annually by the over 200-year old United States Pharmacopeial Convention (usually also called the USP), a nonprofi ...
XXII published in 1992 was the first to specify limits for 34 named
pesticide Pesticides are substances that are used to control pests. They include herbicides, insecticides, nematicides, fungicides, and many others (see table). The most common of these are herbicides, which account for approximately 50% of all p ...
s. A total limit of 40  ppm (i.e. 40 mg/kg) total pesticides was stipulated for lanolin of general use, with no individual limit greater than 10 ppm. A second monograph also introduced into the US Pharmacopoeia XXII in 1992 was entitled 'Modified Lanolin'. Lanolin conforming to this monograph is intended for use in more exacting applications, for example on open wounds. In this monograph, the limit of total pesticides was reduced to 3 ppm total pesticides, with no individual limit greater than 1 ppm. In 2000, the
European Pharmacopoeia The ''European Pharmacopoeia'' (''Pharmacopoeia Europaea'', ''Ph. Eur.'') is a major regional pharmacopoeia which provides common quality standards throughout the pharmaceutical industry in Europe to control the quality of Pharmaceutical drug, ...
introduced pesticide residue limits into its lanolin monograph. This requirement, which is generally regarded as the new quality standard, extends the list of pesticides to 40 and imposes even lower concentration limits. Some very high-purity grades of lanolin surpass monograph requirements. New products obtained using complex purification techniques produce lanolin esters in their natural state, removing oxidative and environmental impurities resulting in white, odourless,
hypoallergenic Hypoallergenic, meaning "below average" or "slightly" allergenic, is a term meaning that something (usually cosmetics, pets, textiles, food, etc.) causes fewer allergic reactions. The term was first used in 1953 in an advertising campaign for co ...
lanolin. These ultra-high-purity grades of lanolin are ideally suited to the treatment of dermatological disorders such as
eczema Dermatitis is a term used for different types of skin inflammation, typically characterized by itchiness, redness and a rash. In cases of short duration, there may be small blisters, while in long-term cases the skin may become thickened ...
and on open wounds. Lanolin attracted attention owing to a misunderstanding concerning its sensitising potential. A study carried out at New York University Hospital in the early 1950s had shown about 1% of patients with dermatological disorders were allergic to the lanolin being used at that time. By one estimate, this simple misunderstanding of failing to differentiate between the general healthy population and patients with dermatological disorders exaggerates the sensitising potential of lanolin by 5,000–6,000 times. The European
Cosmetics Directive Council Directive 76/768/EEC of 27 July 1976 on the approximation of the laws of the Member States relating to cosmetic productsstratum corneum The stratum corneum (Latin language, Latin for 'horny layer') is the outermost layer of the epidermis (skin), epidermis. Consisting of dead tissue, it protects underlying tissue from infection, dehydration, chemicals and mechanical stress. It is ...
lipids; the
lipids Lipids are a broad group of organic compounds which include fats, waxes, sterols, fat-soluble vitamins (such as vitamins Vitamin A, A, Vitamin D, D, Vitamin E, E and Vitamin K, K), monoglycerides, diglycerides, phospholipids, and others. The fu ...
which help regulate the rate of water loss across the
epidermis The epidermis is the outermost of the three layers that comprise the skin, the inner layers being the dermis and Subcutaneous tissue, hypodermis. The epidermal layer provides a barrier to infection from environmental pathogens and regulates the ...
and govern the hydration state of the skin.
Cryogenic In physics, cryogenics is the production and behaviour of materials at very low temperatures. The 13th International Institute of Refrigeration's (IIR) International Congress of Refrigeration (held in Washington, DC in 1971) endorsed a univers ...
scanning electron microscopy A scanning electron microscope (SEM) is a type of electron microscope that produces images of a sample by scanning the surface with a focused beam of electrons. The electrons interact with atoms in the sample, producing various signals that ...
has shown that lanolin, like human stratum corneum lipids, consists of a mass of liquid crystalline material. Cross-polarised light microscopy has shown the multilamellar
vesicle Vesicle may refer to: ; In cellular biology or chemistry * Vesicle (biology and chemistry), a supramolecular assembly of lipid molecules, like a cell membrane * Synaptic vesicle ; In human embryology * Vesicle (embryology), bulge-like features ...
s formed by lanolin are identical to those formed by human stratum corneum lipids. The incorporation of bound water into the stratum corneum involves the formation of multilamellar vesicles. Skin
bioengineering Biological engineering or bioengineering is the application of principles of biology and the tools of engineering to create usable, tangible, economically viable products. Biological engineering employs knowledge and expertise from a number ...
studies have shown the durational effect of the
emollient A moisturizer, or emollient, is a cosmetic preparation used for protecting, moisturizing, and lubricating the skin. These functions are normally performed by sebum produced by healthy skin. The word "emollient" is derived from the Latin verb ''mo ...
(skin smoothing) action produced by lanolin is very significant and lasts for many hours. Lanolin applied to the skin at 2 mg/cm2 has been shown to reduce roughness by about 35% after one hour and 50% after two hours, with the overall effect lasting for considerably more than eight hours. Lanolin is also known to form semiocclusive (breathable) films on the skin. When applied daily at around 4 mg/cm2 for five consecutive days, the positive moisturizing effects of lanolin were detectable until 72 hours after final application. Lanolin may achieve some of its moisturizing effects by forming a secondary moisture reservoir within the skin. The barrier repair properties of lanolin have been reported to be superior to those produced by both
petrolatum Petroleum jelly, petrolatum (), white petrolatum, soft paraffin, or multi-hydrocarbon, CAS number 8009-03-8, is a semi-solid mixture of hydrocarbons (with carbon numbers mainly higher than 25), originally promoted as a Topical medication, topica ...
and
glycerol Glycerol () is a simple triol compound. It is a colorless, odorless, sweet-tasting, viscous liquid. The glycerol backbone is found in lipids known as glycerides. It is also widely used as a sweetener in the food industry and as a humectant in pha ...
. In a small clinical study conducted on volunteer subjects with terribly dry ( xerotic) hands, lanolin was shown to be superior to petrolatum in reducing the signs and symptoms of dryness and
scaling Scaling may refer to: Science and technology Mathematics and physics * Scaling (geometry), a linear transformation that enlarges or diminishes objects * Scale invariance, a feature of objects or laws that do not change if scales of length, energ ...
, cracks and abrasions, and pain and itch. In another study, a high purity grade of lanolin was found to be significantly superior to petrolatum in assisting the healing of superficial wounds.


References


External links

* {{Use dmy dates, date=March 2020 Animal glandular products Waxes Non-petroleum based lubricants By-products