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 * 1Chemical reactions
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LIMONENE

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From Wikipedia, the free encyclopedia

Liquid terpene hydrocarbon fragrance and flavor, extract of citrus peel
Not to be confused with Limonin.



Limonene

Skeletal structure of the (R)-isomer Ball-and-stick model of the (R)-isomer

Names Preferred IUPAC name
1-Methyl-4-(prop-1-en-2-yl)cyclohex-1-ene
Other names
1-Methyl-4-(1-methylethenyl)cyclohexene
4-Isopropenyl-1-methylcyclohexene
p-Menth-1,8-diene
Racemic: DL-Limonene; Dipentene
Identifiers
CAS Number
 * 138-86-3 (R/S) Y
 * 5989-27-5 (R) Y
 * 5989-54-8 (S) Y

3D model (JSmol)
 * Interactive image

ChEBI
 * CHEBI:15384 Y

ChEMBL
 * ChEMBL449062 (R) Y

ChemSpider
 * 20939 (R/S) Y
 * 388386 (S) Y
 * 389747 (R) Y

ECHA InfoCard 100.004.856 KEGG
 * D00194 Y

PubChem CID
 * 22311 (R/S)
 * 439250 (S)

UNII
 * 9MC3I34447 (R/S) Y
 * GFD7C86Q1W (R) Y
 * 47MAJ1Y2NE (S) Y

CompTox Dashboard (EPA)
 * DTXSID2029612

show
InChI
 * InChI=1S/C10H16/c1-8(2)10-6-4-9(3)5-7-10/h4,10H,1,5-7H2,2-3H3 Y
   Key: XMGQYMWWDOXHJM-UHFFFAOYSA-N Y

show
SMILES
 * CC1=CCC(CC1)C(=C)C

Properties
Chemical formula
C10H16 Molar mass 136.238 g·mol−1 Appearance colorless liquid Odor Orange
Density 0.8411 g/cm3 Melting point −74.35 °C (−101.83 °F; 198.80 K) Boiling
point 176 °C (349 °F; 449 K)
Solubility in water
Insoluble Solubility Miscible with benzene, chloroform, ether, CS2, and oils
soluble in CCl4
Chiral rotation ([α]D)
87–102°
Refractive index (nD)
1.4727 Thermochemistry
Std enthalpy of
combustion (ΔcH⦵298)
−6.128 MJ mol−1 Hazards Occupational safety and health (OHS/OSH):
Main hazards
Skin sensitizer / Contact dermatitis – After aspiration, pulmonary oedema,
pneumonitis, and death[1] GHS labelling:
Pictograms
Signal word
Danger
Hazard statements
H226, H304, H315, H317, H410
Precautionary statements
P210, P233, P235, P240, P241, P242, P243, P261, P264, P272, P273, P280,
P301+P330+P331, P302+P352, P303+P361+P353, P304+P340, P312, P333+P313, P362,
P370+P378, P391, P403+P233, P405, P501 NFPA 704 (fire diamond)
2
2
0
Flash point 50 °C (122 °F; 323 K)
Autoignition
temperature
237 °C (459 °F; 510 K)
Except where otherwise noted, data are given for materials in their standard
state (at 25 °C [77 °F], 100 kPa).

Infobox references

Chemical compound

Limonene is a colorless liquid aliphatic hydrocarbon classified as a cyclic
monoterpene, and is the major component in the volatile oil of citrus fruit
peels.[1] The (+)-isomer, occurring more commonly in nature as the fragrance of
oranges, is a flavoring agent in food manufacturing.[1][2] It is also used in
chemical synthesis as a precursor to carvone and as a renewables-based solvent
in cleaning products.[1] The less common (-)-isomer has a piny, turpentine-like
odor, and is found in the edible parts of such plants as caraway, dill, and
bergamot orange plants.[3]

Limonene takes its name from Italian limone ("lemon").[4] Limonene is a chiral
molecule, and biological sources produce one enantiomer: the principal
industrial source, citrus fruit, contains (+)-limonene (d-limonene), which is
the (R)-enantiomer.[1] (+)-Limonene is obtained commercially from citrus fruits
through two primary methods: centrifugal separation or steam distillation.


CHEMICAL REACTIONS[EDIT]

Limonene is a relatively stable monoterpene and can be distilled without
decomposition, although at elevated temperatures it cracks to form isoprene.[5]
It oxidizes easily in moist air to produce carveol, carvone, and limonene
oxide.[1][6] With sulfur, it undergoes dehydrogenation to p-cymene.[7]

Limonene occurs commonly as the (R)-enantiomer, but racemizes at 300 °C. When
warmed with mineral acid, limonene isomerizes to the conjugated diene
α-terpinene (which can also easily be converted to p-cymene). Evidence for this
isomerization includes the formation of Diels–Alder adducts between α-terpinene
adducts and maleic anhydride.

It is possible to effect reaction at one of the double bonds selectively.
Anhydrous hydrogen chloride reacts preferentially at the disubstituted alkene,
whereas epoxidation with mCPBA occurs at the trisubstituted alkene.

In another synthetic method Markovnikov addition of trifluoroacetic acid
followed by hydrolysis of the acetate gives terpineol.

The most widely practiced conversion of limonene is to carvone. The three-step
reaction begins with the regioselective addition of nitrosyl chloride across the
trisubstituted double bond. This species is then converted to the oxime with a
base, and the hydroxylamine is removed to give the ketone-containing carvone.[2]


BIOSYNTHESIS[EDIT]

In nature, limonene is formed from geranyl pyrophosphate, via cyclization of a
neryl carbocation or its equivalent as shown.[8] The final step involves loss of
a proton from the cation to form the alkene.


IN PLANTS[EDIT]

(+)-Limonene is a major component of the aromatic scents and resins
characteristic of numerous coniferous and broadleaved trees: red and silver
maple (Acer rubrum, Acer saccharinum), cottonwoods (Populus angustifolia),
aspens (Populus grandidentata, Populus tremuloides) sumac (Rhus glabra), spruce
(Picea spp.), various pines (e.g., Pinus echinata, Pinus ponderosa), Douglas fir
(Pseudotsuga menziesii), larches (Larix spp.), true firs (Abies spp.), hemlocks
(Tsuga spp.), cannabis (Cannabis sativa spp.),[9] cedars (Cedrus spp.), various
Cupressaceae, and juniper bush (Juniperus spp.).[1][failed verification] It
contributes to the characteristic odor of orange peel, orange juice and other
citrus fruits.[1][10] To optimize recovery of valued components from citrus peel
waste, (+)-limonene is typically removed.[11]


SAFETY AND RESEARCH[EDIT]

(+)-Limonene applied to skin may cause irritation from contact dermatitis, but
otherwise appears to be safe for human uses.[12][13] Limonene is flammable as a
liquid or vapor and it is toxic to aquatic life.[1]


USES[EDIT]

Limonene is common as a dietary supplement and as a fragrance ingredient for
cosmetics products.[1] As the main fragrance of citrus peels, D-limonene is used
in food manufacturing and some medicines, such as a flavoring agent to mask the
bitter taste of alkaloids, and as a fragrance in perfumery, aftershave lotions,
bath products, and other personal care products.[1] (+)-Limonene is also used as
a botanical insecticide.[1][14] (+)-Limonene is used in the organic
herbicides.[15] It is added to cleaning products, such as hand cleansers to give
a lemon or orange fragrance (see orange oil) and for its ability to dissolve
oils.[1] In contrast, (-)-limonene has a piny, turpentine-like odor.

Limonene is used as a solvent for cleaning purposes, such as adhesive remover,
or the removal of oil from machine parts, as it is produced from a renewable
source (citrus essential oil, as a byproduct of orange juice manufacture).[11]
It is used as a paint stripper and is also useful as a fragrant alternative to
turpentine. Limonene is also used as a solvent in some model airplane glues and
as a constituent in some paints. Commercial air fresheners, with air
propellants, containing limonene are used by stamp collectors to remove
self-adhesive postage stamps from envelope paper.[16]

Limonene is also used as a solvent for fused filament fabrication based 3D
printing.[17] Printers can print the plastic of choice for the model, but erect
supports and binders from High Impact Polystyrene (HIPS), a polystyrene plastic
that is easily soluble in limonene.

In preparing tissues for histology or histopathology, D-limonene is often used
as a less toxic substitute for xylene when clearing dehydrated specimens.
Clearing agents are liquids miscible with alcohols (such as ethanol or
isopropanol) and with melted paraffin wax, in which specimens are embedded to
facilitate cutting of thin sections for microscopy.[18][19][20]

Limonene, from orange peel oil, is also combustible and has been considered as a
biofuel.[21]


SEE ALSO[EDIT]

 * Essential oil
 * Monoterpenes
 * Resin


REFERENCES[EDIT]

 1.  ^ Jump up to: a b c d e f g h i j k l m "D-Limonene". PubChem Compound
     Database. National Center for Biotechnology Information, US National
     Library of Medicine. 2017. Retrieved 22 December 2017.
 2.  ^ Jump up to: a b Fahlbusch, Karl-Georg; Hammerschmidt, Franz-Josef;
     Panten, Johannes; et al. (2003). "Flavors and Fragrances". Ullmann's
     Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a11_141.
     ISBN 978-3-527-30673-2.
 3.  ^ "Molecule of the Week Archive: Limonene". ACS.org. American Chemical
     Society. 1 November 2021. Retrieved 5 November 2021.
 4.  ^ "limonene". merriam-webster.com. Merriam-Webster. 22 September 2023.
     Retrieved 23 September 2023.
 5.  ^ Pakdel, H. (2001). "Production of DL-limonene by vacuum pyrolysis of used
     tires". Journal of Analytical and Applied Pyrolysis. 57: 91–107.
     doi:10.1016/S0165-2370(00)00136-4.
 6.  ^ Karlberg, Ann-Therese; Magnusson, Kerstin; Nilsson, Ulrika (1992). "Air
     oxidation of D-limonene (the citrus solvent) creates potent allergens".
     Contact Dermatitis. 26 (5): 332–340.
     doi:10.1111/j.1600-0536.1992.tb00129.x. PMID 1395597. S2CID 46373225.
 7.  ^ Weitkamp, A. W. (1959). "I. The Action of Sulfur on Terpenes. The
     Limonene Sulfides". Journal of the American Chemical Society. 81 (13):
     3430–3434. doi:10.1021/ja01522a069.
 8.  ^ Mann, J. C.; Hobbs, J. B.; Banthorpe, D. V.; Harborne, J. B. (1994).
     Natural Products: Their Chemistry and Biological Significance. Harlow,
     Essex: Longman Scientific & Technical. pp. 308–309. ISBN 0-582-06009-5.
 9.  ^ Booth, Judith K.; Page, Jonathan E.; Bohlmann, Jörg (29 March 2017).
     Hamberger, Björn (ed.). "Terpene synthases from Cannabis sativa". PLOS ONE.
     12 (3): e0173911. Bibcode:2017PLoSO..1273911B.
     doi:10.1371/journal.pone.0173911. ISSN 1932-6203. PMC 5371325.
     PMID 28355238.
 10. ^ Perez-Cacho, Pilar Ruiz; Rouseff, Russell L. (10 July 2008). "Fresh
     squeezed orange juice odor: A review". Critical Reviews in Food Science and
     Nutrition. 48 (7): 681–695. doi:10.1080/10408390701638902. ISSN 1040-8398.
     PMID 18663618. S2CID 32567584.
 11. ^ Jump up to: a b Sharma, Kavita; Mahato, Neelima; Cho, Moo Hwan; Lee, Yong
     Rok (2017). "Converting citrus wastes into value-added products: Economic
     and environmentally friendly approaches". Nutrition. 34: 29–46.
     doi:10.1016/j.nut.2016.09.006. ISSN 0899-9007. PMID 28063510.
 12. ^ Kim, Y.-W.; Kim, M.-J.; Chung, B.-Y.; et al. (2013). "Safety evaluation
     and risk assessment of D-Limonene". Journal of Toxicology and Environmental
     Health, Part B. 16 (1): 17–38. doi:10.1080/10937404.2013.769418.
     PMID 23573938. S2CID 40274650.
 13. ^ Deza, Gustavo; García Bravo, Begoña; Silvestre, Juan F.; et al. (2017).
     "Contact sensitization to limonene and linalool hydroperoxides in Spain: A
     GEIDAC prospective study" (PDF). Contact Dermatitis. 76 (2): 74–80.
     doi:10.1111/cod.12714. hdl:10230/33527. PMID 27896835. S2CID 21494625.
 14. ^ "Limonene" (PDF). EPA.gov. United States Environmental Protection Agency.
     September 1994. Archived from the original (PDF) on 16 October 2014.
     Retrieved 7 January 2022.
 15. ^ "Safety Data Sheet". Cutting Edge Formulations, Inc. 14 November 2014.
     Retrieved 7 January 2022 – via wsimg.com.
 16. ^ Butler, Peter (October 2010). "It's Like Magic; Removing Self-Adhesive
     Stamps from Paper" (PDF). American Philatelist. American Philatelic
     Society. 124 (10): 910–913.
 17. ^ "Using D-Limonene to Dissolve 3D Printing Support Structures".
     fargo3dprinting.com. Fargo 3D Printing. 26 April 2014. Retrieved 30
     December 2015.
 18. ^ Wynnchuk, Maria (1994). "Evaluation of Xylene Substitutes for a Paraffin
     Tissue Processing". Journal of Histotechnology (2): 143–149.
     doi:10.1179/014788894794710913 – via ingentaconnect.com.
 19. ^ Carson, F. (1997). Histotechnology: A Self-Instructional Text. Chicago:
     ASCP Press. pp. 28–31. ISBN 0-89189-411-X.
 20. ^ Kiernan, J. A. (2008). Histological and Histochemical Methods (4th ed.).
     Bloxham, Oxon. pp. 54, 57. ISBN 978-1-904842-42-2.{{cite book}}: CS1 maint:
     location missing publisher (link)
 21. ^ "Cyclone Power to Showcase External Combustion Engine at SAE Event".
     greencarcongress.com. Green Car Congress. 20 September 2007.


EXTERNAL LINKS[EDIT]

 * Mass spectrum of limonene
 * Description of D-limonene on the International Chemical Safety Cards
 * D-Limonene information from the United States Environmental Protection Agency



show
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 * e

Citrus
True species
 * Australian and Papuan wild limes
 * Citron
 * Clymenia
 * Ichang papeda
 * Kaffir lime
 * Kumquats
 * Common mandarin
 * Mangshanyegan
 * Mountain citron
 * Pomelo
 * Ryukyu mandarin

Major hybrids
 * Grapefruit
 * Lemon
 * Lime
 * Orange

True and hybrid
cultivars
 * Alemow
 * Amanatsu
 * Assam lemon
 * Bergamot orange
 * Bizzaria
 * Bitter orange
 * Blood lime
 * Blood orange
 * Byeonggyul
 * Biasong
 * Cam sành
 * Cara cara navel
 * Citrange
 * Citrumelo
 * Clementine
 * Coorg orange
 * Daidai
 * Dekopon
 * Encore
 * Fairchild tangerine
 * Florentine citron
 * Forbidden fruit
 * Ginger lime
 * Haruka
 * Hassaku orange
 * Hebesu
 * Heen naran
 * Hyuganatsu
 * Imperial lemon
 * Indian wild orange
 * Iyokan
 * Jabara
 * Jaffa orange
 * Jamaican tangelo
 * Kabbad
 * Kabosu
 * Kakadu lime
 * Kalpi
 * Kanpei
 * Kawachi Bankan
 * Key lime
 * Khasi papeda
 * Kinkoji unshiu
 * Kinnow
 * Kishu mikan
 * Kiyomi
 * Kobayashi mikan
 * Koji
 * Komikan
 * Kuchinotsu No. 37
 * Laraha
 * Lemonade fruit
 * Limón de Pica
 * Lumia
 * Mandelo
 * Mandora
 * Melanesian papeda
 * Melogold
 * Meyer lemon
 * Micrantha
 * Midknight Valencia Orange
 * Murcott
 * Myrtle-leaved orange tree
 * Nagpur orange
 * Nasnaran
 * New Zealand grapefruit
 * Ōgonkan
 * Orangelo/Chironja
 * Oroblanco
 * Palestinian sweet lime
 * Persian lime
 * Pixie mandarin
 * Pompia
 * Ponderosa lemon
 * Ponkan
 * Rangpur
 * Reikou
 * Rhobs el Arsa
 * Rough lemon
 * Samuyao
 * Sanbokan
 * Satsuma mandarin
 * Setoka
 * Shangjuan
 * Shonan Gold
 * Smith Red Valencia
 * Sudachi
 * Suruga yuko
 * Sweet lemon
 * Sweet limetta
 * Tangelo
 * Tangerine
 * Tangor
 * Valencia orange
 * Variegated pink lemon
 * Volkamer lemon
 * Winged lime
 * Xã Đoài orange
 * Yūkō
 * Yuzu

Citrons
 * Balady citron
 * Corsican citron
 * Diamante citron
 * Fingered citron/Buddha's hand
 * Greek citron
 * Moroccan citron
 * Yemenite citron

Mandarin oranges
 * Cleopatra mandarin
 * Shīkwāsā
 * Nanfengmiju
 * Tachibana
 * Willowleaf orange

Papedas
 * Celebes papeda
 * Citrus halimii/Mountain "citron"
 * Ichang papeda

Pomelos
 * Banpeiyu
 * Dangyuja

Kumquat hybrids (× Citrofortunella)
 * Calamansi
 * Citrangequat
 * Limequat
 * Mandarinquat
 * Procimequat
 * Sunquat
 * Yuzuquat

Sahul citrus
(former Microcitrus, Eromocitrus,
Clymenia and Oxanthera genera)
 * Australian outback lime
 * Australian round lime
 * Brown River finger lime
 * Desert lime
 * Maiden's wild lime
 * Mount White lime (Microcitrus)
 * New Guinea wild lime
 * Russell River lime
 * Clymenia
 * Orange-flowered oxanthera
 * Large-leaf oxanthera
 * Wavy-leaf oxanthera
 * Oxanthera brevipes

Related genera
(perhaps properly Citrus)
 * Poncirus/Trifoliate orange

Drinks
 * Calamansi juice
 * Chūhai
 * Curaçao
 * Dried lime tea (noomi basra)
 * Grapefruit juice
 * Lemonade
 * Limeade
 * Orange juice
 * Yuja-hwachae
 * Yuja tea

Products
 * Calcium citrate
 * Citric acid
 * Lemonene
 * Limonene
 * Neroli
 * Orange flower water
 * Orange oil
 * Orangeat
 * Succade
 * Zest

Diseases
 * Black spot
 * Canker
 * CTV/Tristeza
 * Exocortis
 * Greening
 * Mal secco
 * Phytophthora
   * citricola

Citrus botanists
 * Clara H. Hasse
 * Robert Willard Hodgson
 * Lena B. Smithers Hughes
 * David Mabberley
 * Clément Rodier
 * Robert Soost
 * Walter Tennyson Swingle
 * Chōzaburō Tanaka
 * Ikuro Takahashi
 * Johann Christoph Volkamer
 * Herbert John Webber

Related topics
 * The Citrus Industry
 * Citrus production
 * Citrus rootstock
 * Citrus taxonomy
 * Cold-hardy citrus
 * Hesperidium
 * Japanese citrus
 * List of citrus fruits
 * Mother Orange Tree
 * Orangery
 * University of California Citrus Experiment Station
 * University of California, Riverside Citrus Variety Collection

 * Category
 * Production
 * Commons



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Types of terpenes and terpenoids (# of isoprene units)
Basic forms:
 * Acyclic (linear, cis and trans forms)
 * Monocyclic (single ring)
 * Bicyclic (2 rings)
 * Iridoids (cyclopentane ring)
 * Iridoid glycosides (iridoids bound to a sugar)
 * Steroids (4 rings)

Hemiterpenoids (1)
 * Isoprene (C5H8)
 * Prenol
 * Isovaleric acid

Monoterpenes (C10H16)(2)


Acyclic
 * Ocimene
 * Myrcenes

Monocyclic
 * Limonene
 * Terpinene
 * Phellandrene

Bicyclic
 * Pinene (α and β)
 * Camphene
 * Thujene
 * Sabinene
 * Carene


Monoterpenoids (2,modified)


Acyclic
 * Citronellal
 * Citral
 * Citronellol
 * Geraniol
 * Geranyl pyrophosphate
 * Halomon
 * Linalool

Monocyclic
 * Grapefruit mercaptan
 * Menthol
 * p-Cymene
 * Thujaplicins (Hinokitiol)
 * Thymol
 * Perillyl alcohol
 * Carvacrol

Bicyclic
 * Camphor
 * Borneol
 * Bornyl acetate
 * Eucalyptol
 * Ascaridole
 * Umbellulone


Sesquiterpenoids (3)
 * Artemisinin
 * Bisabolol
 * Cadinene
 * Cadinol
 * Cedrene
 * Chanootin
 * Farnesyl pyrophosphate
 * Juniperol
 * Longifolene
 * Muurolene
 * Nootkatin

Diterpenoids (4)


Acyclic
 * Phytol
 * Geranylgeranyl pyrophosphate
 * Geranyl-linalool

Monocyclic
 * Retinol
 * Retinal

Bicyclic
 * cis-Abienol
 * Epimanool
 * Salvinorin A

Tricyclic
 * Cembrene
 * Forskolin
 * Manoyl oxide
 * Pimaral
 * Pimarol

Tetracyclic
 * Aphidicolin
 * Gibberellin
 * Paclitaxel

Resin acids
 * Abietic acid
 * Communic acid
 * Dehydroabietic acid
 * Isopimaric acid
 * Lambertianic acid
 * Levopimaric acid
 * Mercusic acid
 * Neoabietic acid
 * Pimaric acid
 * Sandaracopimaric acid
 * Secodehydroabietic acid
 * Palustric acid


Sesterterpenoids (5)
 * Geranylfarnesol

Triterpenoids (6)


Steroids
 * Phytosterols
   * Campesterol
   * Citrostadienol
   * Cycloartenol
   * Sitostanol
   * Sitosterol
   * Stigmasterol
 * Tocopherols
 * Cholesterol
 * Testosterone
 * Cholecalciferol
 * Ecdysones

Other
 * Betulin
 * Lanosterol
 * Saponins
 * Serratenediol
 * Squalane
 * Acids
   * Oleanolic acid
   * Ursolic acid
   * Betulinic acid
   * Moronic acid


Sesquarterpenes/oids (7)
 * Ferrugicadiol
 * Tetraprenylcurcumene

Tetraterpenoids
(Carotenoids) (8)


Carotenes
 * Alpha-Carotene
 * Beta-Carotene
 * Gamma-Carotene
 * Delta-Carotene
 * Lycopene
 * Neurosporene
 * Phytofluene
 * Phytoene

Xanthophylls:
 * Canthaxanthin
 * Cryptoxanthin
 * Zeaxanthin
 * Astaxanthin
 * Lutein
 * Rubixanthin


Polyterpenoids (many)
 * Rubber
 * Gutta percha
 * Gutta-balatá

Norisoprenoids (modified)
 * 3-oxo-α-ionol
 * 7,8-dihydroionone

Synthesis
 * Terpene synthase enzymes (many), having in common a terpene synthase N
   terminal domain (protein domain)

Activated isoprene forms
 * Isopentenyl pyrophosphate (IPP)
 * Dimethylallyl pyrophosphate (DMAPP)

Retrieved from
"https://en.wikipedia.org/w/index.php?title=Limonene&oldid=1189288377"
Categories:
 * Flavors
 * Histotechnology
 * Hydrocarbon solvents
 * IARC Group 3 carcinogens
 * Insecticides
 * Monoterpenes
 * Solvents
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