Isobornyl acetate

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Isobornyl acetate
Isobornyl acetate.svg
Names
IUPAC name
[(1S,2S,4S)-1,7,7-trimethyl-2-bicyclo[2.2.1]heptanyl] acetate
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.004.298 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 204-727-6
PubChem CID
RTECS number
  • NP7350000
  • 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/t9-,10-,12+/m0/s1
    Key: KGEKLUUHTZCSIP-JBLDHEPKSA-N
  • CC(=O)O[C@H]1C[C@@H]2CC[C@]1(C2(C)C)C
Properties
C12H20O2
Molar mass 196.290 g·mol−1
Appearancecolorless liquid
Density 0.9841 g/cm3
Boiling point 102–103 °C (216–217 °F; 375–376 K) 13 torr
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Isobornyl acetate is an organic compound consisting of the acetate ester or the terpenoid isoborneol. It is a colorless liquid with a pleasant pine-like scent, and it is produced on a multi-ton scale for this purpose. The compound is prepared by reaction of camphene with acetic acid in the presence of a strongly acidic catalyst such as sulfuric acid. Hydrolysis of isobornyl acetate gives isoborneol, a precursor to camphor. [1]

Like many plant exudates, isobornyl acetate appears to have antifeedant properties. [2]

Related Research Articles

In chemistry, a salt is a chemical compound consisting of an ionic assembly of positively charged cations and negatively charged anions, which results in a compound with no net electric charge. A common example is table salt, with positively charged sodium ions and negatively charged chloride ions.

<span class="mw-page-title-main">Acetate</span> Salt compound formed from acetic acid and a base

An acetate is a salt formed by the combination of acetic acid with a base. "Acetate" also describes the conjugate base or ion typically found in aqueous solution and written with the chemical formula C
2
H
3
O
2
. The neutral molecules formed by the combination of the acetate ion and a positive ion are also commonly called "acetates". The simplest of these is hydrogen acetate with corresponding salts, esters, and the polyatomic anion CH
3
CO
2
, or CH
3
COO
.

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

Ethyl acetate is the organic compound with the formula CH3CO2CH2CH3, simplified to C4H8O2. This colorless liquid has a characteristic sweet smell and is used in glues, nail polish removers, and in the decaffeination process of tea and coffee. Ethyl acetate is the ester of ethanol and acetic acid; it is manufactured on a large scale for use as a solvent.

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

Acetic anhydride, or ethanoic anhydride, is the chemical compound with the formula (CH3CO)2O. Commonly abbreviated Ac2O, it is the simplest isolable anhydride of a carboxylic acid and is widely used as a reagent in organic synthesis. It is a colorless liquid that smells strongly of acetic acid, which is formed by its reaction with moisture in the air.

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

Sodium acetate, CH3COONa, also abbreviated NaOAc, is the sodium salt of acetic acid. This colorless deliquescent salt has a wide range of uses.

<span class="mw-page-title-main">Borneol</span> Chemical compound Borneol, Sesquterpene, found in different varieties of Cannabis.

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">Copper(II) acetate</span> Chemical compound

Copper(II) acetate, also referred to as cupric acetate, is the chemical compound with the formula Cu(OAc)2 where AcO is acetate (CH
3
CO
2
). The hydrated derivative, Cu2(OAc)4(H2O)2, which contains one molecule of water for each copper atom, is available commercially. Anhydrous copper(II) acetate is a dark green crystalline solid, whereas Cu2(OAc)4(H2O)2 is more bluish-green. Since ancient times, copper acetates of some form have been used as fungicides and green pigments. Today, copper acetates are used as reagents for the synthesis of various inorganic and organic compounds. Copper acetate, like all copper compounds, emits a blue-green glow in a flame.

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

Calcium acetate is a chemical compound which is a calcium salt of acetic acid. It has the formula Ca(C2H3O2)2. Its standard name is calcium acetate, while calcium ethanoate is the systematic name. An older name is acetate of lime. The anhydrous form is very hygroscopic; therefore the monohydrate (Ca(CH3COO)2•H2O) is the common form.

<span class="mw-page-title-main">Chromium(II) acetate</span> Chemical compound

Chromium(II) acetate hydrate, also known as chromous acetate, is the coordination compound with the formula Cr2(CH3CO2)4(H2O)2. This formula is commonly abbreviated Cr2(OAc)4(H2O)2. This red-coloured compound features a quadruple bond. The preparation of chromous acetate once was a standard test of the synthetic skills of students due to its sensitivity to air and the dramatic colour changes that accompany its oxidation. It exists as the dihydrate and the anhydrous forms.

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

Isoborneol is a bicyclic organic compound and a terpene derivative. The hydroxyl group in this compound is placed in an exo position. The endo diastereomer is called borneol. Being chiral, isoborneol exists as enantiomers.

<span class="mw-page-title-main">Toilet Duck</span> Brand of toilet cleaner

Toilet Duck is a brand name of toilet cleaner noted for the duck-shape of its bottle shaped to assist in dispensing the cleaner under the rim. The design was patented in 1980 by Walter Düring from Dällikon, Switzerland. It is now produced by S. C. Johnson & Son.

<span class="mw-page-title-main">Lead(IV) acetate</span> Organometallic compound (Pb(C2H3O2)4)

Lead(IV) acetate or lead tetraacetate is an organometallic compound with chemical formula Pb(C2H3O2)4. It is a colorless solid that is soluble in nonpolar, organic solvents, indicating that it is not a salt. It is degraded by moisture and is typically stored with additional acetic acid. The compound is used in organic synthesis.

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

Trenbolone acetate, sold under brand names such as Finajet and Finaplix among others, is an androgen and anabolic steroid (AAS) medication which is used in veterinary medicine, specifically to increase the profitability of livestock by promoting muscle growth in cattle. It is given by injection into muscle.

<span class="mw-page-title-main">Rhodium(II) acetate</span> Chemical compound

Rhodium(II) acetate is the coordination compound with the formula Rh2(AcO)4, where AcO is the acetate ion (CH
3
CO
2
). This dark green powder is slightly soluble in polar solvents, including water. It is used as a catalyst for cyclopropanation of alkenes. It is a widely studied example of a transition metal carboxylate complex.

<span class="mw-page-title-main">2-Ethylhexanoic acid</span> Chemical compound

2-Ethylhexanoic acid is the organic compound with the formula CH3(CH2)3CH(C2H5)CO2H. It is a carboxylic acid that is widely used to prepare lipophilic metal derivatives that are soluble in nonpolar organic solvents. 2-Ethylhexanoic acid is a colorless viscous oil. It is supplied as a racemic mixture.

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

Oxyphenisatine is a laxative. It is closely related to bisacodyl, sodium picosulfate, and phenolphthalein. Long-term use is associated with liver damage, and as a result, it was withdrawn in most countries in the early 1970s. The acetate derivative oxyphenisatine acetate was also once used as a laxative.

<span class="mw-page-title-main">Acetic acid</span> Colorless and faint organic acid found in vinegar

Acetic acid, systematically named ethanoic acid, is an acidic, colourless liquid and organic compound with the chemical formula CH3COOH. Vinegar is at least 4% acetic acid by volume, making acetic acid the main component of vinegar apart from water and other trace elements.

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

Anhydrous magnesium acetate has the chemical formula Mg(C2H3O2)2 and in its hydrated form, magnesium acetate tetrahydrate, it has the chemical formula Mg(CH3COO)2 • 4H2O. In this compound magnesium has an oxidation state of 2+. Magnesium acetate is the magnesium salt of acetic acid. It is deliquescent and upon heating, it decomposes to form magnesium oxide. Magnesium acetate is commonly used as a source of magnesium in biological reactions.

Rhodoferax is a genus of Betaproteobacteria belonging to the purple nonsulfur bacteria. Originally, Rhodoferax species were included in the genus Rhodocyclus as the Rhodocyclus gelatinous-like group. The genus Rhodoferax was first proposed in 1991 to accommodate the taxonomic and phylogenetic discrepancies arising from its inclusion in the genus Rhodocyclus. Rhodoferax currently comprises four described species: R. fermentans, R. antarcticus, R. ferrireducens, and R. saidenbachensis. R. ferrireducens, lacks the typical phototrophic character common to two other Rhodoferax species. This difference has led researchers to propose the creation of a new genus, Albidoferax, to accommodate this divergent species. The genus name was later corrected to Albidiferax. Based on geno- and phenotypical characteristics, A. ferrireducens was reclassified in the genus Rhodoferax in 2014. R. saidenbachensis, a second non-phototrophic species of the genus Rhodoferax was described by Kaden et al. in 2014.

<span class="mw-page-title-main">Neodymium acetate</span> Compound of neodymium

Neodymium acetate is an inorganic salt composed of a neodymium atom trication and three acetate groups as anions where neodymium exhibits the +3 oxidation state. It has a chemical formula of Nd(CH3COO)3 although it can be informally referred to as NdAc because Ac is an informal symbol for acetate. It commonly occurs as a light purple powder.

References

  1. Panten, Johannes; Surburg, Horst (2015). "Flavors and Fragrances, 2. Aliphatic Compounds". Ullmann's Encyclopedia of Industrial Chemistry. pp. 1–55. doi:10.1002/14356007.t11_t01. ISBN   9783527306732.
  2. Andrews, R. E.; Parks, L. W.; Spence, K. D. (1980). "Some Effects of Douglas Fir Terpenes on Certain Microorganisms". Applied and Environmental Microbiology. 40 (2): 301–304. Bibcode:1980ApEnM..40..301A. doi:10.1128/aem.40.2.301-304.1980. PMC   291570 . PMID   16345609.