Camphene

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title: "Camphene" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["vinylidene-compounds", "perfume-ingredients", "flavors", "monoterpenes", "bicyclic-compounds", "cyclopentanes", "terpenes-and-terpenoids"] topic_path: "general/vinylidene-compounds" source: "https://en.wikipedia.org/wiki/Camphene" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

| Watchedfields = changed | verifiedrevid = 443755477 | Reference= | Name = Camphene | ImageFileL1 = Camphene.png | ImageFileR1 = Camphene_BS.png | ImageName = Camphene | PIN = 2,2-Dimethyl-3-methylidenebicyclo[2.2.1]heptane | OtherNames = 2,2-Dimethyl-3-methanylidenebicyclo[2.2.1]heptane 2,2-Dimethyl-3-methylenebicyclo[2.2.1]heptane |Section1={{Chembox Identifiers | ChemSpiderID_Ref = | ChemSpiderID = 6364 | PubChem = 6616 | KEGG_Ref = | KEGG = C06076 | InChI = 1/C10H16/c1-7-8-4-5-9(6-8)10(7,2)3/h8-9H,1,4-6H2,2-3H3 | InChIKey = CRPUJAZIXJMDBK-UHFFFAOYAL | StdInChI_Ref = | StdInChI = 1S/C10H16/c1-7-8-4-5-9(6-8)10(7,2)3/h8-9H,1,4-6H2,2-3H3 | StdInChIKey_Ref = | StdInChIKey = CRPUJAZIXJMDBK-UHFFFAOYSA-N | CASNo_Ref = | CASNo1 = 79-92-5 | CASNo1_Comment = racemate | CASNo2 = 5794-03-6] | CASNo2_Comment = + enantiomer | CASNo3 = 5794-04-7 | CASNo3_Comment = - enantiomer | UNII_Ref = | UNII = G3VG94Z26E | ChEBI_Ref = | ChEBI = 3830 | ChEMBL = 2268550 | RTECS = EX1055000 | UNNumber = 2319 1325 | SMILES = C1(=C)C(C)(C)C2CC1CC2 | EINECS = 201-234-8 |Section2={{Chembox Properties | C=10|H=16 | Appearance = White or colorless solid | Density = 0.842 g/cm3 | MeltingPtC = 51 to 52 | MeltingPt_ref = | BoilingPtC = 159 | BoilingPt_ref = | Solubility = Practically insoluble |Section3={{Chembox Hazards | FlashPtC = 40 | GHSPictograms = | GHSSignalWord = Warning | HPhrases = | PPhrases =

Camphene is a bicyclic organic compound. It is one of the most pervasive monoterpenes. As with other terpenes, it is insoluble in water, flammable, colorless, and has a pungent smell. It is a minor constituent of many essential oils such as turpentine, cypress oil, camphor oil, citronella oil, neroli, ginger oil, valerian, and mango. It is produced industrially by isomerization of the more common alpha-pinene using a solid acid catalyst such as titanium dioxide.

Camphene is used in the preparation of fragrances and as a food additive for flavoring. These include isobornyl acetate.

Biosynthesis

Camphene is biosynthesized from linalyl pyrophosphate via a sequence of carbocationic intermediates. :[[File:CampheneBiosyn.svg|thumb|394px|Biosynthesis of camphene (one enantiomer) from linalyl pyrophosphate.|left]]

References

References

  1. ''[[Merck Index]]'', 11th Edition, '''1736'''
  2. (2000). "Terpenes".
  3. (2005). "Volatile Components from Mango (Mangifera indicaL.) Cultivars". Journal of Agricultural and Food Chemistry.
  4. (2006). "Kirk-Othmer Encyclopedia of Chemical Technology".
  5. (1988). "Biosynthesis of Monoterpenes. Enantioselectivity in the Enzymatic Cyclization of (+)- and (-)-Linalyl Pyrophosphate to (+)- and (-)-Pinene and (+)- and (-)-Camphene". The Journal of Biological Chemistry.

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vinylidene-compoundsperfume-ingredientsflavorsmonoterpenesbicyclic-compoundscyclopentanesterpenes-and-terpenoids