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Citronellal information


Citronellal[1]
Skeletal formula of (+)-citronellal
Ball-and-stick model of the (+)-citronellal molecule
(+)-Citronellal
Ball-and-stick model of the (-)-citronellal molecule
(-)-Citronellal
Names
IUPAC name
3,7-dimethyloct-6-enal
Identifiers
CAS Number
  • 106-23-0 checkY
3D model (JSmol)
  • Interactive image
  • Interactive image
Beilstein Reference
1209447 1720789
ChEBI
  • CHEBI:47856 checkY
ChEMBL
  • ChEMBL447944 checkY
ChemSpider
  • 7506 checkY
ECHA InfoCard 100.003.070 Edit this at Wikidata
EC Number
  • 203-376-6
Gmelin Reference
1521962
KEGG
  • C17384 checkY
PubChem CID
  • 7794
UNII
  • QB99VZZ7GZ checkY
CompTox Dashboard (EPA)
  • DTXSID3041790 Edit this at Wikidata
InChI
  • InChI=1S/C10H18O/c1-9(2)5-4-6-10(3)7-8-11/h5,8,10H,4,6-7H2,1-3H3 checkY
    Key: NEHNMFOYXAPHSD-UHFFFAOYSA-N checkY
  • 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
SMILES
  • C/C(C)=C/CCC(C)CC=O
  • O=CCC(CC/C=C(/C)C)C
Properties
Chemical formula
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:
Pictograms
GHS07: Exclamation mark GHS09: Environmental hazard[2]
Signal word
Warning
Hazard statements
H315, H317, H411[2]
Precautionary statements
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).
checkY verify (what is checkY☒N ?)
Infobox references

Citronellal or rhodinal (C10H18O) 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]

  1. ^ Citronellal, The Merck Index, 12th Edition
  2. ^ a b c 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) CS1 maint: numeric names: authors list (link)

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Citronellal

Last Update:

Citronellal or rhodinal (C10H18O) is a monoterpenoid aldehyde, the main component in the mixture of terpenoid chemical compounds that give citronella...

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Citronella oil

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The oil is used extensively as a source of perfumery chemicals such as citronellal, citronellol, and geraniol. These chemicals find extensive use in soap...

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Hydroxycitronellal

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used in perfumery. Its molecular formula is C10H20O2. It derives from a citronellal. 7-Hydroxy-3, 7-dimethyloctanal, also known as 3, 7-dimethyl-7-hydroxyoctan-1-al...

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Kaffir lime

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of citronellal, whereas its enantiomer, (+)-(R)-citronellal is found in both lemon balm and (to a lesser degree) lemon grass, (however, citronellal is...

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Sichuan pepper

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-forschung A, 206, 228, 1998) Zanthoxylum piperitum (Japan [leaves]) — citronellal, citronellol, Z-3-hexenal (Bioscience, Biotechnology, and Biochemistry...

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Citral

Last Update:

compound, has a less intense but sweeter lemon note.) The aldehydes citronellal and citral are considered key components responsible for the lemon note...

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Corymbia citriodora

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Australia. The essential oil of the lemon-scented gum mainly consists of citronellal (80%), produced largely in Brazil and China. Unrefined oil from the lemon...

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Kumquat

Last Update:

26%); ketones such as carvone (0.175%); and a range of aldehydes such as citronellal (0.6%) and 2-methylundecanal. Other oxygenated compounds include nerol...

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Lemon balm

Last Update:

geranial (4–85%) (both isomers of citral), (E)-caryophyllene (0–14%), and citronellal (1–44%). It is also one of the ingredients in Spreewald gherkins. Melissa...

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Macrocycle

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illustrative macrocyclization is the synthesis of (−)-muscone from (+)-citronellal. The 15-membered ring is generated by ring-closing metathesis. One important...

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Muscone

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asymmetric synthesis of (−)-muscone begins with commercially available (+)-citronellal, and forms the 15-membered ring via ring-closing metathesis: A more recent...

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Terpene

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readily obtainable from natural sources, is converted to citronellal and camphor. Citronellal is also converted to rose oxide and menthol. Eberhard Breitmaier...

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Citronella

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2007 album None Shall Pass All pages with titles containing Citronella Citronellal, a component in the compounds that give citronella oil its distinctive...

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Natural rubber

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Acyclic Citronellal Citral Citronellol Geraniol Geranyl pyrophosphate Halomon Linalool Monocyclic Grapefruit mercaptan Menthol p-Cymene Thujaplicins (Hinokitiol)...

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Limonene

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Acyclic Citronellal Citral Citronellol Geraniol Geranyl pyrophosphate Halomon Linalool Monocyclic Grapefruit mercaptan Menthol p-Cymene Thujaplicins (Hinokitiol)...

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Steroid

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Acyclic Citronellal Citral Citronellol Geraniol Geranyl pyrophosphate Halomon Linalool Monocyclic Grapefruit mercaptan Menthol p-Cymene Thujaplicins (Hinokitiol)...

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Terpenoid

Last Update:

Monoterpenoids Monoterpenes 2 10 C10H16 Bornyl acetate, camphor, carvone, citral, citronellal, citronellol, geraniol, eucalyptol, hinokitiol, iridoids, linalool, menthol...

Word Count : 642

Menthol

Last Update:

BINAP rhodium complex to give (after hydrolysis) enantiomerically pure R-citronellal. This is cyclised by a carbonyl-ene-reaction initiated by zinc bromide...

Word Count : 2865

Zanthoxylum piperitum

Last Update:

Oriental Healing Arts Institute. p. 382. ISBN 9780941942225., "..citral, citronellal, dipentene; (+)-phellandrene, geraniol;(2)pungent substances: sanshool...

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Hexahydrocannabinol

Last Update:

research groups have successfully synthesized (+)-HHC and (-)-HHC using citronellal and olivetol, as well as other related compounds. HHC and related hydrogenated...

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Cymbopogon citratus

Last Update:

amazonensis. Lemon grass oil contains 65–85% citral in addition to myrcene, citronellal, citronellol, linalool and geraniol. Hydrosteam distillation, condensation...

Word Count : 1299

Myrcene

Last Update:

flavor and fragrance chemicals, such as menthol, citral, citronellol, citronellal, geraniol, nerol, and linalool. Both myrcene and myrcenol undergo Diels-Alder...

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C10H18O

Last Update:

molecular formula C10H18O (molar mass : 154.25 g/mol) may refer to: Borneol Citronellal Eucalyptol 2-Decenal Fenchol Geraniol Grandisol Lavandulol Linalool Menthone...

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Backhousia citriodora

Last Update:

myrtle oil is typically 90–98%, and oil yield 1–3% from fresh leaf. The citronellal chemotype is uncommon, and can be used as an insect repellent. The dried...

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Capsaicin

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Acyclic Citronellal Citral Citronellol Geraniol Geranyl pyrophosphate Halomon Linalool Monocyclic Grapefruit mercaptan Menthol p-Cymene Thujaplicins (Hinokitiol)...

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Dietary fiber

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Acyclic Citronellal Citral Citronellol Geraniol Geranyl pyrophosphate Halomon Linalool Monocyclic Grapefruit mercaptan Menthol p-Cymene Thujaplicins (Hinokitiol)...

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Monoterpene

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Additional rearrangements and oxidations provide compounds such as citral, citronellal, citronellol, linalool, and many others. Many monoterpenes found in marine...

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Citronellol

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dermal safety, citronellol has been evaluated as an insect repellent. Citronellal Geraniol Rhodinol Pelargonium graveolens Perfume intolerance (allergy)...

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Cholecalciferol

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Acyclic Citronellal Citral Citronellol Geraniol Geranyl pyrophosphate Halomon Linalool Monocyclic Grapefruit mercaptan Menthol p-Cymene Thujaplicins (Hinokitiol)...

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