Bornyl acetate

Last updated
Bornyl acetate
Bornyl acetate.svg
Names
Preferred IUPAC name
1,7,7-Trimethylbicyclo[2.2.1]heptan-2-yl acetate
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ECHA InfoCard 100.000.878 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 200-964-4
KEGG
PubChem CID
RTECS number
  • NP7350000
UNII
  • InChI=1S/C12H20O2/c1-8(13)14-10-7-9-5-6-12(10,4)11(9,2)3/h9-10H,5-7H2,1-4H3
    Key: KGEKLUUHTZCSIP-UHFFFAOYSA-N
  • CC(=O)OC1CC2CCC1(C2(C)C)C
Properties
C12H20O2
Molar mass 196.290 g·mol−1
Melting point 27–29 °C
Boiling point 223–224 °C
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Bornyl acetate is a chemical compound. [1] Its molecular formula is C12H20O2 and its molecular weight is 196.29 g/mol. It is the acetate ester of borneol. It is used as a food additive, [2] flavouring agent, and odour agent.

It is a component of the essential oil from pine needles (from the family Pinaceae) [3] [4] [5] and primarily responsible for its odor. [6]

Related Research Articles

<span class="mw-page-title-main">Essential oil</span> Hydrophobic liquid containing volatile aroma compounds from plants

An essential oil is a concentrated hydrophobic liquid containing volatile chemical compounds from plants. Essential oils are also known as volatile oils, ethereal oils, aetheroleum, or simply as the oil of the plant from which they were extracted, such as oil of clove. An essential oil is essential in the sense that it contains the essence of the plant's fragrance—the characteristic fragrance of the plant from which it is derived. The term "essential" used here does not mean indispensable or usable by the human body, as with the terms essential amino acid or essential fatty acid, which are so called because they are nutritionally required by a living organism.

<span class="mw-page-title-main">Lavender oil</span> Essential oil distilled from lavender flower spikes

Lavender oil is an essential oil obtained by distillation from the flower spikes of certain species of lavender. There are over 400 types of lavender worldwide with different scents and qualities. Two forms of lavender oil are distinguished, lavender flower oil, a colorless oil, insoluble in water, having a density of 0.885 g/mL; and lavender spike oil, a distillate from the herb Lavandula latifolia, having a density of 0.905 g/mL. Like all essential oils, it is not a pure compound; it is a complex mixture of phytochemicals, including linalool and linalyl acetate.

<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.

<i>Cedrus deodara</i> Species of plant

Cedrus deodara, the deodar cedar, Himalayan cedar, or deodar, is a species of cedar native to the Himalayas.

<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">Anethole</span> Chemical compound

Anethole is an organic compound that is widely used as a flavoring substance. It is a derivative of the aromatic compound allylbenzene and occurs widely in plants in essential oils. It is in the class of phenylpropanoid organic compounds. It contributes a large component of the odor and flavor of anise and fennel, anise myrtle (Myrtaceae), liquorice (Fabaceae), magnolia blossoms, and star anise (Schisandraceae). Closely related to anethole is its isomer estragole, which is abundant in tarragon (Asteraceae) and basil (Lamiaceae), and has a flavor reminiscent of anise. It is a colorless, fragrant, mildly volatile liquid. Anethole is only slightly soluble in water but exhibits high solubility in ethanol. This trait causes certain anise-flavored liqueurs to become opaque when diluted with water; this is called the ouzo effect.

<span class="mw-page-title-main">Limonene</span> Liquid terpene hydrocarbon fragrance and flavor, extract of citrus peel

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. The (+)-isomer, occurring more commonly in nature as the fragrance of oranges, is a flavoring agent in food manufacturing. It is also used in chemical synthesis as a precursor to carvone and as a renewables-based solvent in cleaning products. 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.

<span class="mw-page-title-main">Rose oil</span> Essential oil extracted from rose petals

Rose oil is the essential oil extracted from the petals of various types of rose. Rose ottos are extracted through steam distillation, while rose absolutes are obtained through solvent extraction, the absolute being used more commonly in perfumery. The production technique originated in Greater Iran. Even with their high price and the advent of organic synthesis, rose oils are still perhaps the most widely used essential oil in perfumery.

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

Eucalyptol is a monoterpenoid colorless liquid, and a bicyclic ether. It has a fresh camphor-like odor and a spicy, cooling taste. It is insoluble in water, but miscible with organic solvents. Eucalyptol makes up about 70–90% of eucalyptus oil. Eucalyptol forms crystalline adducts with hydrohalic acids, o-cresol, resorcinol, and phosphoric acid. Formation of these adducts is useful for purification.

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

Borneol is a bicyclic organic compound and a terpene derivative. The hydroxyl group in this compound is placed in an endo position. The exo diastereomer is called isoborneol. Being chiral, borneol exists as enantiomers, both of which are found in nature.

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

Caryophyllene, more formally (−)-β-caryophyllene,(BCP), is a natural bicyclic sesquiterpene that is a constituent of many essential oils, especially clove oil, the oil from the stems and flowers of Syzygium aromaticum (cloves), the essential oil of Cannabis sativa, copaiba, rosemary, and hops. It is usually found as a mixture with isocaryophyllene (the cis double bond isomer) and α-humulene (obsolete name: α-caryophyllene), a ring-opened isomer. Caryophyllene is notable for having a cyclobutane ring, as well as a trans-double bond in a 9-membered ring, both rarities in nature.

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

Sabinene is a natural bicyclic monoterpene with the molecular formula C10H16. It is isolated from the essential oils of a variety of plants including Marjoram, holm oak (Quercus ilex) and Norway spruce (Picea abies). It has a strained ring system with a cyclopentane ring fused to a cyclopropane ring.

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

Humulene, also known as α-humulene or α-caryophyllene, is a naturally occurring monocyclic sesquiterpene (C15H24), containing an 11-membered ring and consisting of 3 isoprene units containing three nonconjugated C=C double bonds, two of them being triply substituted and one being doubly substituted. It was first found in the essential oils of Humulus lupulus (hops), from which it derives its name. Humulene is an isomer of β-caryophyllene, and the two are often found together as a mixture in many aromatic plants.

α-Pinene Chemical compound

α-Pinene is an organic compound of the terpene class. It is one of the two isomers of pinene, the other being β-pinene. An alkene, it contains a reactive four-membered ring. It is found in the oils of many species of many coniferous trees, notably the pine. It is also found in the essential oil of rosemary and Satureja myrtifolia. Both enantiomers are known in nature; (1S,5S)- or (−)-α-pinene is more common in European pines, whereas the (1R,5R)- or (+)-α-isomer is more common in North America. The enantiomers' racemic mixture is present in some oils such as eucalyptus oil and orange peel oil.

Rose hip seed oil is a pressed seed oil, extracted from the seeds of the wild rose bush Rosa rubiginosa in the southern Andes. Rosehip seed oil can also be extracted from Rosa canina, a wild rose species native to Europe, northwest Africa, and western Asia. The fruits of the rosehip have been used in folk medicine for a long time. Rosehips have prophylactic and therapeutic actions against the common cold, infectious diseases, gastrointestinal disorders, urinary tract diseases, and inflammatory diseases.

<i>Curcuma caesia</i> Species of flowering plant

Curcuma caesia, black turmeric or black zedoary, is a perennial herb with bluish-black rhizomes that is native to northeast India.

α-Cadinol Chemical compound

α-Cadinol or 10α-hydroxy-4-cadinene is an organic compound, a sesquiterpenoid alcohol.

<span class="mw-page-title-main">Bergamot essential oil</span> Cold-pressed essential oil

Bergamot essential oil is a cold-pressed essential oil produced by cells inside the rind of a bergamot orange fruit. It is a common flavoring and top note in perfumes. The scent of bergamot essential oil is similar to a sweet light orange peel oil with a floral note.

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

Acetyleugenol is a phenylpropanoid compound found in cloves. It is the second in abundance to the related compound eugenol in certain extract preparations. Like eugenol, its found in several plants such as Acacia nilotica and Piper betle and has similar antibacterial and antifungal properties on C. albicans and S. mutans. It inhibits aggregation of platelets and has partial agonistic activity on AhR.

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

Pinocarveol is an organic compound with the formula C10H16O. It is a bicyclic monoterpenoid, which is a combination of two isoprene units with one hydroxyl group as a substituent. It exists as either trans- or cis-pinocarveol, referring to stereochemical orientation of the oxygen as compared to the methylene bridge. It is a naturally occurring molecule in numerous plant species including Eucalyptus globulus and Picea abies. Pinocarveol is found in a variety of essential oils.

References

  1. CID 6448 from PubChem
  2. "Code of Federal Regulations Title 21".
  3. Lee, Na-Hyun; Lee, Sang-Min; Lee, Tae-Min; Chung, Namhyun; Lee, Hoi-Seon (2015). "GC-MS Analyses of the Essential Oils Obtained from Pinaceae Leaves in Korea". Journal of Essential Oil Bearing Plants. 18 (3): 538. doi:10.1080/0972060X.2013.764194. S2CID   93566094.
  4. Garneau, François-Xavier; Collin, Guy; Gagnon, Hélène; Pichette, André (2012). "Chemical Composition of the Hydrosol and the Essential Oil of Three Different Species of the Pinaceae Family :Picea glauca(Moench) Voss.,Picea mariana(Mill.) B.S.P., and Abies balsamea(L.) Mill". Journal of Essential Oil Bearing Plants. 15 (2): 227. doi:10.1080/0972060X.2012.10644040. S2CID   94394684.
  5. Karapandzova, M; Stefkova, G; Cvetkovikj, I; Trajkovska-Dokik, E; Kaftandzieva, A; Kulevanova, S (2014). "Chemical composition and antimicrobial activity of the essential oils of Pinus peuce (Pinaceae) growing wild in R. Macedonia". Natural Product Communications. 9 (11): 1623–8. doi: 10.1177/1934578X1400901124 . PMID   25532297.
  6. Ullmann's Food and Feed. Vol. 2. Wiley-VCH. 2017-06-19. p. 1193. ISBN   9783527339907. Pinaceae needle oils from Pinaceae species contain (-)-bornyl acetate as their main odoriferous component.