Carvacrol
Encyclopedia
Carvacrol, or cymophenol, C6H3CH3(OH)(C3H7), is a monoterpenoid
phenol. It has a characteristic pungent, warm odor of oregano
and a pizza-like taste.
of Origanum vulgare, oil of thyme
, oil obtained from pepperwort
, and wild bergamot
. The essential oil of Thyme
subspecies contains between 5% and 75% of carvacrol, while Satureja (savory) subspecies have a content between 1% and 45%. The Origanum
species majorana
and Dittany of Crete are rich in carvacrol, 50% resp. 60-80%.
strains, e.g. Escherichia coli
and Bacillus cereus
. Its low toxicity together with its pleasant taste and smell suggests its use as a food additive
to prevent bacterial contamination. In Pseudomonas aeruginosa
it causes damages to the cell membrane
of these bacteria and, unlike other terpenes, inhibits the proliferation of this germ. The cause of the antimicrobial properties is believed to be disruption of the bacteria membrane.
It is a potent activator of the human ion channels transient receptor potential V3 (TRPV3
) and A1 (TRPA1
). Application of carvacrol on the human tongue, as well as activation of TRPV3, causes a sensation of warmth. In addition carvacrol also activates, but rapidly desensitizes
the pain receptor TRPA1 explaining its pungency.
It activates PPAR and suppresses COX-2 inflammation .
In rats carvacrol is quickly metabolized and excreted. The main metabolic route is ester
ification of the phenol
ic group with sulfuric acid
and glucuronic acid
. A minor pathway is oxidation of the terminal methyl groups to primary alcohols. After 24 hours only very small amounts of carvacrol or its metabolites could be found in urine, indicating an almost complete excretion within one day.
with caustic potash
; by the action of nitrous acid
on 1-methyl-2-amino-4-propyl benzene
; by prolonged heating of five parts of camphor
with one part of iodine
; or by heating carvol with glacial phosphoric acid
or by performing a dehydrogenation
of carvone
with a Pd/C catalyst. It is extracted from Origanum oil by means of a 50% potash solution. It is a thick oil which sets at 20 °C to a mass of crystals of melting point 0°C, and boiling point 236-237 °C. Oxidation with ferric chloride converts it into dicarvacrol, whilst phosphorus pentachloride transforms it into chlorcymol.
risks. The cytotoxic ability of carvacrol on prooxidant activity can make it an effective antiseptic and antimicrobial agent.
Carvacrol has been found to show antioxidant
activity.
Antimicrobial
activity:
Monoterpene
Monoterpenes are a class of terpenes that consist of two isoprene units and have the molecular formula C10H16. Monoterpenes may be linear or contain rings...
phenol. It has a characteristic pungent, warm odor of oregano
Oregano
Oregano – scientifically named Origanum vulgare by Carolus Linnaeus – is a common species of Origanum, a genus of the mint family . It is native to warm-temperate western and southwestern Eurasia and the Mediterranean region.Oregano is a perennial herb, growing from 20–80 cm tall,...
and a pizza-like taste.
Natural occurrence
Carvacrol is present in the essential oilEssential oil
An essential oil is a concentrated hydrophobic liquid containing volatile aroma compounds from plants. Essential oils are also known as volatile oils, ethereal oils or aetherolea, or simply as the "oil of" the plant from which they were extracted, such as oil of clove...
of Origanum vulgare, oil of thyme
Thyme
Thyme is a culinary and medicinal herb of the genus Thymus.-History:Ancient Egyptians used thyme for embalming. The ancient Greeks used it in their baths and burnt it as incense in their temples, believing it was a source of courage...
, oil obtained from pepperwort
Pepperwort
Lepidium latifolium, known by several common names including Broadleaved Pepperweed, Pepperwort, or Peppergrass, Dittander, Dittany, and Tall Whitetop, is a perennial plant that is a member of the mustard and cabbage family.This plant is native to southern Europe, Mediterranean countries and Asia...
, and wild bergamot
Bergamot
Bergamot may refer to:*The Bergamot orange*Monarda, genus of herbs of similar odor to the Bergamot orange; in particular**Monarda didyma, called Bergamot, Scarlet Beebalm, Scarlet Monarda, Oswego Tea, or Crimson Beebalm...
. The essential oil of Thyme
Thyme
Thyme is a culinary and medicinal herb of the genus Thymus.-History:Ancient Egyptians used thyme for embalming. The ancient Greeks used it in their baths and burnt it as incense in their temples, believing it was a source of courage...
subspecies contains between 5% and 75% of carvacrol, while Satureja (savory) subspecies have a content between 1% and 45%. The Origanum
Origanum
Origanum is a genus of about 20 species of aromatic herbs in the family Lamiaceae, native to the Mediterranean region east to eastern Asia...
species majorana
Majorana
Majorana may refer to:* Majorana equation, a relativistic wave equation* Majorana fermion, a concept in particle physics* Majorana spinor, a concept in quantum field theory* Origanum majorana, a somewhat cold-sensitive perennial herb...
and Dittany of Crete are rich in carvacrol, 50% resp. 60-80%.
Biological properties and use
Carvacrol inhibits the growth of several bacteriaBacteria
Bacteria are a large domain of prokaryotic microorganisms. Typically a few micrometres in length, bacteria have a wide range of shapes, ranging from spheres to rods and spirals...
strains, e.g. Escherichia coli
Escherichia coli
Escherichia coli is a Gram-negative, rod-shaped bacterium that is commonly found in the lower intestine of warm-blooded organisms . Most E. coli strains are harmless, but some serotypes can cause serious food poisoning in humans, and are occasionally responsible for product recalls...
and Bacillus cereus
Bacillus cereus
Bacillus cereus is an endemic, soil-dwelling, Gram-positive, rod-shaped, beta hemolytic bacterium. Some strains are harmful to humans and cause foodborne illness, while other strains can be beneficial as probiotics for animals...
. Its low toxicity together with its pleasant taste and smell suggests its use as a food additive
Food additive
Food additives are substances added to food to preserve flavor or enhance its taste and appearance.Some additives have been used for centuries; for example, preserving food by pickling , salting, as with bacon, preserving sweets or using sulfur dioxide as in some wines...
to prevent bacterial contamination. In Pseudomonas aeruginosa
Pseudomonas aeruginosa
Pseudomonas aeruginosa is a common bacterium that can cause disease in animals, including humans. It is found in soil, water, skin flora, and most man-made environments throughout the world. It thrives not only in normal atmospheres, but also in hypoxic atmospheres, and has, thus, colonized many...
it causes damages to the cell membrane
Cell membrane
The cell membrane or plasma membrane is a biological membrane that separates the interior of all cells from the outside environment. The cell membrane is selectively permeable to ions and organic molecules and controls the movement of substances in and out of cells. It basically protects the cell...
of these bacteria and, unlike other terpenes, inhibits the proliferation of this germ. The cause of the antimicrobial properties is believed to be disruption of the bacteria membrane.
It is a potent activator of the human ion channels transient receptor potential V3 (TRPV3
TRPV3
Transient receptor potential cation channel, subfamily V, member 3, also known as TRPV3, is a human gene encoding the protein of the same name.- Physiology of TRPV3 channel :...
) and A1 (TRPA1
TRPA1
Transient receptor potential cation channel, subfamily A, member 1, also known as TRPA1, is a protein which in humans is encoded by the TRPA1 gene....
). Application of carvacrol on the human tongue, as well as activation of TRPV3, causes a sensation of warmth. In addition carvacrol also activates, but rapidly desensitizes
Desensitation
In telecommunication, desensitation is the reduction of desired signal gain as a result of receiver reaction to an undesired signal.The gain reduction is generally due to overload of some portion of the receiver resulting in desired signal suppression because the receiver will no longer respond...
the pain receptor TRPA1 explaining its pungency.
It activates PPAR and suppresses COX-2 inflammation .
In rats carvacrol is quickly metabolized and excreted. The main metabolic route is ester
Ester
Esters are chemical compounds derived by reacting an oxoacid with a hydroxyl compound such as an alcohol or phenol. Esters are usually derived from an inorganic acid or organic acid in which at least one -OH group is replaced by an -O-alkyl group, and most commonly from carboxylic acids and...
ification of the phenol
Phenol
Phenol, also known as carbolic acid, phenic acid, is an organic compound with the chemical formula C6H5OH. It is a white crystalline solid. The molecule consists of a phenyl , bonded to a hydroxyl group. It is produced on a large scale as a precursor to many materials and useful compounds...
ic group with sulfuric acid
Sulfuric acid
Sulfuric acid is a strong mineral acid with the molecular formula . Its historical name is oil of vitriol. Pure sulfuric acid is a highly corrosive, colorless, viscous liquid. The salts of sulfuric acid are called sulfates...
and glucuronic acid
Glucuronic acid
Glucuronic acid is a carboxylic acid. Its structure is similar to that of glucose. However, glucuronic acid's sixth carbon is oxidized to a carboxylic acid...
. A minor pathway is oxidation of the terminal methyl groups to primary alcohols. After 24 hours only very small amounts of carvacrol or its metabolites could be found in urine, indicating an almost complete excretion within one day.
Synthesis and derivatives
Carvacrol may be synthetically prepared by the fusion of cymol sulfonic acidSulfonic acid
Sulfonic acid usually refers to a member of the class of organosulfur compounds with the general formula RS2–OH, where R is an alkyl or aryl. The formal part of acid, HS2–OH, are formally derivatives of the "parent" inorganic compound with the formula HSO2.-Preparation:Sulfonic acid is...
with caustic potash
Potash
Potash is the common name for various mined and manufactured salts that contain potassium in water-soluble form. In some rare cases, potash can be formed with traces of organic materials such as plant remains, and this was the major historical source for it before the industrial era...
; by the action of nitrous acid
Nitrous acid
Nitrous acid is a weak and monobasic acid known only in solution and in the form of nitrite salts.Nitrous acid is used to make diazides from amines; this occurs by nucleophilic attack of the amine onto the nitrite, reprotonation by the surrounding solvent, and double-elimination of water...
on 1-methyl-2-amino-4-propyl benzene
Benzene
Benzene is an organic chemical compound. It is composed of 6 carbon atoms in a ring, with 1 hydrogen atom attached to each carbon atom, with the molecular formula C6H6....
; by prolonged heating of five parts of camphor
Camphor
Camphor is a waxy, white or transparent solid with a strong, aromatic odor. It is a terpenoid with the chemical formula C10H16O. It is found in wood of the camphor laurel , a large evergreen tree found in Asia and also of Dryobalanops aromatica, a giant of the Bornean forests...
with one part of iodine
Iodine
Iodine is a chemical element with the symbol I and atomic number 53. The name is pronounced , , or . The name is from the , meaning violet or purple, due to the color of elemental iodine vapor....
; or by heating carvol with glacial phosphoric acid
Phosphoric acid
Phosphoric acid, also known as orthophosphoric acid or phosphoric acid, is a mineral acid having the chemical formula H3PO4. Orthophosphoric acid molecules can combine with themselves to form a variety of compounds which are also referred to as phosphoric acids, but in a more general way...
or by performing a dehydrogenation
Dehydrogenation
Dehydrogenation is a chemical reaction that involves the elimination of hydrogen . It is the reverse process of hydrogenation. Dehydrogenation reactions may be either large scale industrial processes or smaller scale laboratory procedures....
of carvone
Carvone
Carvone is a member of a family of chemicals called terpenoids. Carvone is found naturally in many essential oils, but is most abundant in the oils from seeds of caraway and dill.-Stereoisomerism and odor:...
with a Pd/C catalyst. It is extracted from Origanum oil by means of a 50% potash solution. It is a thick oil which sets at 20 °C to a mass of crystals of melting point 0°C, and boiling point 236-237 °C. Oxidation with ferric chloride converts it into dicarvacrol, whilst phosphorus pentachloride transforms it into chlorcymol.
List of the plants that contain the chemical
- Origanum compactum
- Origanum dictamnusOriganum dictamnusOriganum dictamnus , known in Greek as Δίκταμο or in Cretan dialect Έρωντας , is a tender perennial plant that grows 20–30 cm high...
- Origaum microphyllum
- Origanum onites ,
- Origanum scabrum
- Origanum vulgare ,
- Thymus glandulosus
Toxicology
Carvacrol, like other essential oils, does not have many long-term genotoxicGenotoxic
In genetics, genotoxicity describes a deleterious action on a cell's genetic material affecting its integrity. This includes both certain chemical compounds and certain types of radiation....
risks. The cytotoxic ability of carvacrol on prooxidant activity can make it an effective antiseptic and antimicrobial agent.
Carvacrol has been found to show antioxidant
Antioxidant
An antioxidant is a molecule capable of inhibiting the oxidation of other molecules. Oxidation is a chemical reaction that transfers electrons or hydrogen from a substance to an oxidizing agent. Oxidation reactions can produce free radicals. In turn, these radicals can start chain reactions. When...
activity.
Antimicrobial
Antimicrobial
An anti-microbial is a substance that kills or inhibits the growth of microorganisms such as bacteria, fungi, or protozoans. Antimicrobial drugs either kill microbes or prevent the growth of microbes...
activity:
- 25 different periodontopathic bacteria and strains
- Cladosporium herbarum
- Penicillium glabrum
- Fungi such as F. moniliforme, R. solani, S. sclerotirum, and P. capisci