Citronellal

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Contents

Citronellal [1]
Structural formula of (RS)-Citronellal.svg
(+)-Citronellal 3D ball.png
(+)-Citronellal
(-)-Citronellal 3D ball.png
(-)-Citronellal
Names
IUPAC name
3,7-dimethyloct-6-enal
Identifiers
3D model (JSmol)
1209447 1720789
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.003.070 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 203-376-6
1521962
KEGG
PubChem CID
UNII
  • InChI=1S/C10H18O/c1-9(2)5-4-6-10(3)7-8-11/h5,8,10H,4,6-7H2,1-3H3 Yes check.svgY
    Key: NEHNMFOYXAPHSD-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C10H18O/c1-9(2)5-4-6-10(3)7-8-11/h5,8,10H,4,6-7H2,1-3H3
    Key: NEHNMFOYXAPHSD-UHFFFAOYAH
  • C/C(C)=C/CCC(C)CC=O
  • O=CCC(CC/C=C(/C)C)C
Properties
C10H18O
Molar mass 154.25 g/mol
Density 0.855 g/cm3
Boiling point 201 to 207 °C (394 to 405 °F; 474 to 480 K)
Hazards
GHS labelling:
GHS-pictogram-exclam.svg GHS-pictogram-pollu.svg [2]
Warning
H315, H317, H411 [2]
P262, P273, P280, P302+P352 [2]
Related compounds
Related alkenals
Citral

Methacrolein
trans-2-Methyl-2-butenal

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Yes check.svgY  verify  (what is  Yes check.svgYX mark.svgN ?)

Citronellal or rhodinal (C 10 H 18 O) is a monoterpenoid aldehyde, the main component in the mixture of terpenoid chemical compounds that give citronella oil its distinctive lemon scent.

Citronellal is a main isolate in distilled oils from the plants Cymbopogon (excepting C. citratus, culinary lemongrass), [3] lemon-scented gum, and lemon-scented teatree. The (S)-(−)-enantiomer of citronellal makes up to 80% of the oil from kaffir lime leaves and is the compound responsible for its characteristic aroma.

Citronellal has insect repellent properties, and research shows high repellent effectiveness against mosquitoes. [4] Another research shows that citronellal has strong antifungal qualities. [5]

Compendial status

See also

Related Research Articles

<i>Cymbopogon</i> Genus of grasses

Cymbopogon, also known as lemongrass, barbed wire grass, silky heads, oily heads, Cochin grass, Malabar grass, citronella grass or fever grass, is a genus of Asian, African, Australian, and tropical island plants in the grass family. Some species are commonly cultivated as culinary and medicinal herbs because of their scent, resembling that of lemons . The name cymbopogon derives from the Greek words kymbe and pogon "which mean [that] in most species, the hairy spikelets project from boat-shaped spathes." Lemongrass and its oil are believed to possess therapeutic properties.

Citronella may refer to:

<span class="mw-page-title-main">Citronella oil</span> Fragrant essential oil derived from lemongrass

Citronella oil is an essential oil obtained from the leaves and stems of different species of Cymbopogon (lemongrass). The oil is used extensively as a source of perfumery chemicals such as citronellal, citronellol, and geraniol. These chemicals find extensive use in soap, candles and incense, perfumery, cosmetic, and flavouring industries throughout the world. Citronella oil is also a plant-based insect repellent and has been registered for this use in the United States since 1948. The United States Environmental Protection Agency considers oil of citronella as a biopesticide with a non-toxic mode of action.

<span class="mw-page-title-main">Geraniol</span> Monoterpenoid and alcohol that is the primary component of citronella oil

Geraniol is a monoterpenoid and an alcohol. It is the primary component of citronella oil and is a primary component of rose oil, palmarosa oil. It is a colorless oil, although commercial samples can appear yellow. It has low solubility in water, but it is soluble in common organic solvents. The functional group derived from geraniol is called geranyl.

<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">Insect repellent</span> Substance which repels insects

An insect repellent is a substance applied to the skin, clothing, or other surfaces to discourage insects from landing or climbing on that surface. Insect repellents help prevent and control the outbreak of insect-borne diseases such as malaria, Lyme disease, dengue fever, bubonic plague, river blindness, and West Nile fever. Pest animals commonly serving as vectors for disease include insects such as flea, fly, and mosquito; and ticks (arachnids).

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

Citral is an acyclic monoterpene aldehyde. Being a monoterpene, it is made of two isoprene units. Citral is a collective term which covers two geometric isomers that have their own separate names; the E-isomer is named geranial or citral A. The Z-isomer is named neral or citral B. These stereoisomers occur as a mixture, not necessarily racemic; e.g. in essential oil of Australian ginger, the neral to geranial ratio is 0.61.

<i>Backhousia citriodora</i> Species of tree

Backhousia citriodora is a flowering plant in the family Myrtaceae, genus Backhousia. It is endemic to subtropical rainforests of central and south-eastern Queensland, Australia, with a natural distribution from Mackay to Brisbane.

<span class="mw-page-title-main">Citronellol</span> Pair of enantiomers

Citronellol, or dihydrogeraniol, is a natural acyclic monoterpenoid. Both enantiomers occur in nature. (+)-Citronellol, which is found in citronella oils, including Cymbopogon nardus (50%), is the more common isomer. (−)-Citronellol is widespread, but particularly abundant in the oils of rose (18–55%) and Pelargonium geraniums.

<span class="mw-page-title-main">Eucalyptus oil</span> Distilled oil from the leaf of Eucalyptus

Eucalyptus oil is the generic name for distilled oil from the leaf of Eucalyptus, a genus of the plant family Myrtaceae native to Australia and cultivated worldwide. Eucalyptus oil has a history of wide application, as a pharmaceutical, antiseptic, repellent, flavouring, fragrance and industrial uses. The leaves of selected Eucalyptus species are steam distilled to extract eucalyptus oil.

<i>Pelargonium graveolens</i> Species of plant

Pelargonium graveolens is a Pelargonium species native to the Cape Provinces and the Northern Provinces of South Africa, Zimbabwe and Mozambique.

<i>Corymbia citriodora</i> Species of plant

Corymbia citriodora, commonly known as lemon-scented gum and other common names, is a species of tall tree that is endemic to north-eastern Australia. It has smooth white to pink bark, narrow lance-shaped to curved adult leaves, flower buds in groups of three, white flowers and urn-shaped or barrel-shaped fruit.

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

Nootkatone is a natural organic compound, a sesquiterpenoid, and a ketone that is the most important and expensive aromatic of grapefruit, and which also occurs in other organisms.

<i>Pelargonium</i> citrosum Flowering plant cultivar

Pelargonium 'citrosum' is a perennial subshrub with fragrant leaves that are reminiscent of citronella.

<i>Cymbopogon citratus</i> Species of plant

Cymbopogon citratus, commonly known as West Indian lemon grass or simply lemon grass, is a tropical plant native to Maritime Southeast Asia and introduced to many tropical regions.

<i>p</i>-Menthane-3,8-diol Chemical compound found in oil of lemon eucalyptus

p-Menthane-3,8-diol, also known as para-menthane-3,8-diol, PMD, or menthoglycol, is an organic compound classified as a diol and a terpenoid. It is colorless. Its name reflects the hydrocarbon backbone, which is that of p-menthane. A total of eight stereoisomers are possible, based on the three stereocenters of the ring. Depending on the source, one or more may predominate.

<i>Cymbopogon martinii</i> Species of grass

Cymbopogon martinii is a species of grass in the genus Cymbopogon (lemongrasses) native to India and Indochina but widely cultivated in many places for its aromatic oil. It is best known by the common name palmarosa as it smells sweet and rose-like. Other common names include Indian geranium, gingergrass, rosha, and rosha grass.

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

Cedrol is a sesquiterpene alcohol found in the essential oil of conifers, especially in the genera Cupressus (cypress) and Juniperus (juniper). It has also been identified in Origanum onites, a plant related to oregano. Its main uses are in the chemistry of aroma compounds. It makes up about 19% of cedarwood oil Texas and 15.8% of cedarwood oil Virginia.

<span class="mw-page-title-main">Micro-atmosphere method</span>

The micro-atmosphere method is an antimicrobial testing method involving the use of potentially bacteriostatic or fungicidal compounds which are obtained from the volatile oils of plants, such as citronella grass. This method involves the use of essential oils, a growth medium, a selection of bacterial or cultures and an incubator.

References

  1. Citronellal, The Merck Index, 12th Edition
  2. 1 2 3 Record of Citronellal in the GESTIS Substance Database of the Institute for Occupational Safety and Health, accessed on 13 March 2020.
  3. Mahalwal, Vijender S.; Ali, Mohd. (2003). "Volatile constituents of Cymbopogon nardus (Linn.) Rendle". Flavour and Fragrance Journal. 18: 73–76. doi: 10.1002/ffj.1144 .
  4. Jeong-Kyu KIM; Chang-Soo KANG; Jong-Kwon LEE; Young-Ran KIM; Hye-Yun HAN; Hwa Kyung YUN (2005). "Evaluation of Repellency Effect of Two Natural Aroma Mosquito Repellent Compounds, Citronella and Citronellal". Entomological Research. 35 (2): 117–120. doi:10.1111/j.1748-5967.2005.tb00146.x. S2CID   85112045.
  5. Kazuhiko NAKAHARA, Najeeb S. ALZOREKY1, Tadashi YOSHIHASHI, Huong T. T. NGUYEN and Gassinee TRAKOONTIVAKORN (2003). "Chemical Composition and Antifungal Activity of Essential Oil from Cymbopogon nardus (Citronella Grass)". JARQ. 37 (4).{{cite journal}}: CS1 maint: multiple names: authors list (link)
  6. The British Pharmacopoeia Secretariat (2009). "Index, BP 2009" (PDF). Archived from the original (PDF) on 11 April 2009. Retrieved 31 March 2010.