Nerolidol

Last updated
trans-Nerolidol (top) and cis-Nerolidol (bottom) [1]
Nerolidol.png
Nerolidol - cis.png
Names
IUPAC name
3,7,11-Trimethyl-1,6,10-dodecatrien-3-ol
Other names
Peruviol
Identifiers
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.027.816 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • (unspecified):InChI=1S/C15H26O/c1-6-15(5,16)12-8-11-14(4)10-7-9-13(2)3/h6,9,11,16H,1,7-8,10,12H2,2-5H3
    Key: FQTLCLSUCSAZDY-UHFFFAOYSA-N
  • (cis):InChI=1S/C15H26O/c1-6-15(5,16)12-8-11-14(4)10-7-9-13(2)3/h6,9,11,16H,1,7-8,10,12H2,2-5H3/b14-11-
    Key: FQTLCLSUCSAZDY-KAMYIIQDSA-N
  • (trans):InChI=1S/C15H26O/c1-6-15(5,16)12-8-11-14(4)10-7-9-13(2)3/h6,9,11,16H,1,7-8,10,12H2,2-5H3/b14-11+
    Key: FQTLCLSUCSAZDY-SDNWHVSQSA-N
  • (unspecified):OC(\C=C)(CCC=C(CC/C=C(\C)C)C)C
  • (cis):OC(\C=C)(CC\C=C(/CC/C=C(\C)C)C)C
  • (trans):CC(=CCC/C(=C/CCC(C)(C=C)O)/C)C
Properties
C15H26O
Molar mass 222.37 g/mol
Density 0.872 g/cm3
Boiling point 122 °C (252 °F; 395 K) at 3 mmHg
1.4898
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Nerolidol, also known as peruviol and penetrol , is a naturally occurring sesquiterpene alcohol. A colorless liquid, it is found in the essential oils of many types of plants and flowers. [1] There are four isomers of nerolidol', which differ in the geometry about the central double bond and configuration of the hydroxyl-bearing carbon, but most applications use such a mixture. The aroma of nerolidol is woody and reminiscent of fresh bark. It is used as a flavoring agent and in perfumery as well as in non-cosmetic products such as detergents and cleansers. [2] Nerolidyl derivatives include nerolidyl diphosphate [3] and the fragrance nerolidyl acetate. [4]

Contents

Synthesis and occurrence

Nerolidol is produced commercially from geranylacetone by the addition of vinyl Grignard reagent. It is used as a source of farnesol, vitamin E, and vitamin K1. [4]

Significant sources of natural nerolidol is Cabreuva oil and the oil of Dalbergia parviflora. [4] It is also present in neroli, ginger, jasmine, lavender, tea tree, Cannabis sativa , and lemon grass, and is a dominant scent compound in Brassavola nodosa . [5]

See also

Related Research Articles

<span class="mw-page-title-main">Thujone</span> Group of four possible stereoisomers found in various plants: a.o., absinthe and mint

Thujone is a ketone and a monoterpene that occurs predominantly in two diastereomeric (epimeric) forms: (−)-α-thujone and (+)-β-thujone.

The terpenoids, also known as isoprenoids, are a class of naturally occurring organic chemicals derived from the 5-carbon compound isoprene and its derivatives called terpenes, diterpenes, etc. While sometimes used interchangeably with "terpenes", terpenoids contain additional functional groups, usually containing oxygen. When combined with the hydrocarbon terpenes, terpenoids comprise about 80,000 compounds. They are the largest class of plant secondary metabolites, representing about 60% of known natural products. Many terpenoids have substantial pharmacological bioactivity and are therefore of interest to medicinal chemists.

<span class="mw-page-title-main">Terpene</span> Class of oily organic compounds found in plants

Terpenes are a class of natural products consisting of compounds with the formula (C5H8)n for n ≥ 2. Terpenes are major biosynthetic building blocks. Comprising more than 30,000 compounds, these unsaturated hydrocarbons are produced predominantly by plants, particularly conifers. In plants, terpenes and terpenoids are important mediators of ecological interactions, while some insects use some terpenes as a form of defense. Other functions of terpenoids include cell growth modulation and plant elongation, light harvesting and photoprotection, and membrane permeability and fluidity control.

<span class="mw-page-title-main">Patchouli</span> Species of flowering plant

Patchouli is a species of flowering plant in the family Lamiaceae, commonly called the mint or deadnettle family. The plant grows as a bushy perennial herb, with erect stems reaching up to 75 centimetres (2.5 ft) in height and bearing small, pale, pink-white flowers.

<i>Cannabis sativa</i> Plant species

Cannabis sativa is an annual herbaceous flowering plant. The species was first classified by Carl Linnaeus in 1753. The specific epithet sativa means 'cultivated'. Indigenous to Eastern Asia, the plant is now of cosmopolitan distribution due to widespread cultivation. It has been cultivated throughout recorded history and used as a source of industrial fiber, seed oil, food, and medicine. It is also used as a recreation drug and for religious and spiritual purposes.

<span class="mw-page-title-main">Linalool</span> Chemical compound with a floral aroma

Linalool refers to two enantiomers of a naturally occurring terpene alcohol found in many flowers and spice plants. Linalool has multiple commercial applications, the majority of which are based on its pleasant scent. A colorless oil, linalool is classified as an acyclic monoterpenoid. In plants, it is a metabolite, a volatile oil component, an antimicrobial agent, and an aroma compound. Linalool has uses in manufacturing of soaps, fragrances, food additives as flavors, household products, and insecticides. Esters of linalool are referred to as linalyl, e.g. linalyl pyrophosphate, an isomer of geranyl pyrophosphate.

<span class="mw-page-title-main">Farnesol</span> Chemical compound

Farnesol is a natural 15-carbon organic compound which is an acyclic sesquiterpene alcohol. Under standard conditions, it is a colorless liquid. It is hydrophobic, and thus insoluble in water, but miscible with oils.

<span class="mw-page-title-main">Farnesene</span> Chemical compound

The term farnesene refers to a set of six closely related chemical compounds which all are sesquiterpenes. α-Farnesene and β-farnesene are isomers, differing by the location of one double bond. α-Farnesene is 3,7,11-trimethyl-1,3,6,10-dodecatetraene and β-farnesene is 7,11-dimethyl-3-methylene-1,6,10-dodecatriene. The alpha form can exist as four stereoisomers that differ about the geometry of two of its three internal double bonds. The beta isomer exists as two stereoisomers about the geometry of its central double bond.

Farnesyl pyrophosphate (FPP), also known as farnesyl diphosphate (FDP), is an intermediate in the biosynthesis of terpenes and terpenoids such as sterols and carotenoids. It is also used in the synthesis of CoQ, as well as dehydrodolichol diphosphate.

<span class="mw-page-title-main">Sesquiterpene</span> Class of terpenes

Sesquiterpenes are a class of terpenes that consist of three isoprene units and often have the molecular formula C15H24. Like monoterpenes, sesquiterpenes may be cyclic or contain rings, including many unique combinations. Biochemical modifications such as oxidation or rearrangement produce the related sesquiterpenoids. A recent study conducted in the Cosmics Leaving Outdoor Droplets large cloud chamber at CERN, has identified sesquiterpenes—gaseous hydrocarbons that are released by plants—as potentially playing a major role in cloud formation in relatively pristine regions of the atmosphere.

Monoterpenes are a class of terpenes that consist of two isoprene units and have the molecular formula C10H16. Monoterpenes may be linear (acyclic) or contain rings (monocyclic and bicyclic). Modified terpenes, such as those containing oxygen functionality or missing a methyl group, are called monoterpenoids. Monoterpenes and monoterpenoids are diverse. They have relevance to the pharmaceutical, cosmetic, agricultural, and food industries.

<span class="mw-page-title-main">Cannabis flower essential oil</span> Essential oil obtained from the hemp plant

Cannabis flower essential oil, also known as hemp essential oil, is an essential oil obtained by steam distillation from the flowers, panicles, stem, and upper leaves of the hemp plant. Hemp essential oil is distinct from hemp seed oil and hash oil: the former is a vegetable oil that is cold-pressed from the seeds of low-THC varieties of hemp, the latter is a THC-rich extract of dried female hemp flowers (marijuana) or resin (hashish).

The enzyme (+)-δ-cadinene synthase catalyzes the chemical reaction

The enzyme amorpha-4,11-diene synthase (ADS) catalyzes the chemical reaction

Artemisia pallens, dhavanam from the Sanskrit name दमनक (damanaka),(Tamil: மரிக்கொழுந்து, தவணம், Marathi: दवणा, Kannada: ದವನ), is an aromatic herb, In genus of small herbs or shrubs, xerophytic In nature. The flowers are racemose panicles, bear numerous small yellow flower heads or capitula, but the silvery white silky covering of down gives the foliage a grey or white appearance.

<span class="mw-page-title-main">Absinthin</span> Chemical compound

Absinthin is a naturally produced triterpene lactone from the plant Artemisia absinthium (Wormwood). It constitutes one of the most bitter chemical agents responsible for absinthe's distinct taste. The compound shows biological activity and has shown promise as an anti-inflammatory agent, and should not be confused with thujone, a neurotoxin also found in Artemisia absinthium.

β-Farnesene synthase (EC 4.2.3.47, farnesene synthase, terpene synthase 10, terpene synthase 10-B73, TPS10) is an enzyme with systematic name (2E,6E)-farnesyl-diphosphate diphosphate-lyase ((E)-β-farnesene-forming). This enzyme catalyses the following chemical reaction

(3R,6E)-nerolidol synthase (EC 4.2.3.49, terpene synthase 1) is an enzyme with systematic name (2E,6E)-farnesyl-diphosphate diphosphate-lyase ((3R,6E)-nerolidol-forming). This enzyme catalyses the following chemical reaction

(−)-δ-Cadinene synthase is an enzyme with systematic name (2E,6E)-farnesyl-diphosphate diphosphate-lyase . This enzyme catalyses the following chemical reaction

Geranylacetone is an organic compound with the formula CH3C(O)(CH2)2CH=C(CH3)(CH2)2CH=C(CH3)2. A colorless oil, it is the product of coupling geranyl and acetonyl groups. It is a precursor to synthetic squalene.

References

  1. 1 2 Merck Index , 11th Edition, 6388.
  2. Chan, Weng-Keong; Tan, Loh Teng-Hern; Chan, Kok-Gan; Lee, Learn-Han; Goh, Bey-Hing (2016-04-28). "Nerolidol: A Sesquiterpene Alcohol with Multi-Faceted Pharmacological and Biological Activities". Molecules. 21 (5): 529. doi: 10.3390/molecules21050529 . PMC   6272852 . PMID   27136520.
  3. Benedict, C. R. (1 April 2001). "The Cyclization of Farnesyl Diphosphate and Nerolidyl Diphosphate by a Purified Recombinant delta-Cadinene Synthase". Plant Physiology. 125 (4): 1754–1765. doi:10.1104/pp.125.4.1754. PMC   88832 . PMID   11299356. Open Access logo PLoS transparent.svg
  4. 1 2 3 Sell, Charles S. (2006). "Terpenoids". Kirk-Othmer Encyclopedia of Chemical Technology. doi:10.1002/0471238961.2005181602120504.a01.pub2. ISBN   0471238961.
  5. Kaiser, Roman (1993). The Scent of Orchids. Elsevier. pp. 58, 199–200. ISBN   978-0-444-89841-8.