Benzyl salicylate

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Benzyl salicylate
Benzyl salicylate wide.svg
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Names
Preferred IUPAC name
Benzyl 2-hydroxybenzoate
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.003.876 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C14H12O3/c15-13-9-5-4-8-12(13)14(16)17-10-11-6-2-1-3-7-11/h1-9,15H,10H2 Yes check.svgY
    Key: ZCTQGTTXIYCGGC-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C14H12O3/c15-13-9-5-4-8-12(13)14(16)17-10-11-6-2-1-3-7-11/h1-9,15H,10H2
    Key: ZCTQGTTXIYCGGC-UHFFFAOYAC
  • O=C(OCc1ccccc1)c2ccccc2O
Properties
C14H12O3
Molar mass 228.247 g·mol−1
AppearanceColorless liquid
Density 1.17 g/cm3
Melting point 24 to 25 °C (75 to 77 °F; 297 to 298 K)
Boiling point 318 °C (604 °F; 591 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Benzyl salicylate is a salicylic acid benzyl ester, a chemical compound most frequently used in cosmetics as a fragrance additive or UV light absorber. It appears as an almost colorless liquid with a mild odor described as "very faint, sweet-floral, slightly balsamic" by some, while others smell nothing at all. There is debate whether the odour is caused solely by impurities or a genetic predisposition. [1] It occurs naturally in a variety of plants and plant extracts and is widely used in blends of fragrance materials. [2]

Contents

There is some evidence that people may become sensitized to this material [3] and as a result, there is a restriction standard concerning the use of this material in fragrances by the International Fragrance Association. [4]

It is used as a solvent for crystalline synthetic musks and as a component and fixative in floral perfumes such as carnation, jasmine, lilac, and wallflower. [5]

See also

Related Research Articles

<span class="mw-page-title-main">Benzoic acid</span> Organic compound (C6H5COOH)

Benzoic acid is a white solid organic compound with the formula C6H5COOH, whose structure consists of a benzene ring with a carboxyl substituent. The benzoyl group is often abbreviated "Bz", thus benzoic acid is also denoted as BzOH, since the benzoyl group has the formula –C6H5CO. It is the simplest aromatic carboxylic acid. The name is derived from gum benzoin, which was for a long time its only source.

<span class="mw-page-title-main">Salicylic acid</span> Chemical compound used in medicines and industry

Salicylic acid is an organic compound with the formula HOC6H4COOH. A colorless, bitter-tasting solid, it is a precursor to and a metabolite of aspirin (acetylsalicylic acid). It is a plant hormone, and has been listed by the EPA Toxic Substances Control Act (TSCA) Chemical Substance Inventory as an experimental teratogen. The name is from Latin salix for willow tree, from which it was initially identified and derived. It is an ingredient in some anti-acne products. Salts and esters of salicylic acid are known as salicylates.

Perfume is a mixture of fragrant essential oils or aroma compounds (fragrances), fixatives and solvents, usually in liquid form, used to give the human body, animals, food, objects, and living-spaces an agreeable scent. Perfumes can be defined as substances that emit and diffuse a pleasant and fragrant odor. They consist of manmade mixtures of aromatic chemicals and essential oils. The 1939 Nobel Laureate for Chemistry, Leopold Ružička stated in 1945 that "right from the earliest days of scientific chemistry up to the present time, perfumes have substantially contributed to the development of organic chemistry as regards methods, systematic classification, and theory."

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

Cinnamaldehyde is an organic compound with the formula() C6H5CH=CHCHO. Occurring naturally as predominantly the trans (E) isomer, it gives cinnamon its flavor and odor. It is a phenylpropanoid that is naturally synthesized by the shikimate pathway. This pale yellow, viscous liquid occurs in the bark of cinnamon trees and other species of the genus Cinnamomum. The essential oil of cinnamon bark is about 90% cinnamaldehyde. Cinnamaldehyde decomposes to styrene because of oxidation as a result of bad storage or transport conditions. Styrene especially forms in high humidity and high temperatures. This is the reason why cinnamon contains small amounts of styrene.

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

Methyl salicylate (oil of wintergreen or wintergreen oil) is an organic compound with the formula C8H8O3. It is the methyl ester of salicylic acid. It is a colorless, viscous liquid with a sweet, fruity odor reminiscent of root beer (in which it is used as a flavoring), but often associatively called "minty", as it is an ingredient in mint candies. It is produced by many species of plants, particularly wintergreens. It is also produced synthetically, used as a fragrance and as a flavoring agent.

<span class="mw-page-title-main">Benzyl alcohol</span> Aromatic alcohol

Benzyl alcohol (also known as α-Cresol) is an aromatic alcohol with the formula C6H5CH2OH. The benzyl group is often abbreviated "Bn" (not to be confused with "Bz" which is used for benzoyl), thus benzyl alcohol is denoted as BnOH. Benzyl alcohol is a colorless liquid with a mild pleasant aromatic odor. It is a useful as a solvent for its polarity, low toxicity, and low vapor pressure. Benzyl alcohol has moderate solubility in water (4 g/100 mL) and is miscible in alcohols and diethyl ether. The anion produced by deprotonation of the alcohol group is known as benzylate or benzyloxide.

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

Cinnamic acid is an organic compound with the formula C6H5-CH=CH-COOH. It is a white crystalline compound that is slightly soluble in water, and freely soluble in many organic solvents. Classified as an unsaturated carboxylic acid, it occurs naturally in a number of plants. It exists as both a cis and a trans isomer, although the latter is more common.

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

Piperonal, also known as heliotropin, is an organic compound which is commonly found in fragrances and flavors. The molecule is structurally related to other aromatic aldehydes such as benzaldehyde and vanillin.

<span class="mw-page-title-main">Castoreum</span> Fluid produced by beavers

Castoreum is a yellowish exudate from the castor sacs of mature beavers. Beavers use castoreum in combination with urine to scent mark their territory. Both beaver sexes have a pair of castor sacs and a pair of anal glands, located in two cavities under the skin between the pelvis and the base of the tail. The castor sacs are not true glands on a cellular level, hence references to these structures as preputial glands, castor glands, or scent glands are misnomers.

<span class="mw-page-title-main">Storax balsam</span>

Storax, often commercially sold as styrax, is a natural resin isolated from the wounded bark of Liquidambar orientalis Mill. and Liquidambar styraciflua L. (Hamamelidaceae). It is distinct from benzoin, a similar resin obtained from the Styracaceae plant family.

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

Ethyl salicylate is the ester formed by the condensation of salicylic acid and ethanol. It is a clear liquid that is sparingly soluble in water, but soluble in alcohol and ether. It has a pleasant odor resembling wintergreen and is used in perfumery and artificial flavors.

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

Benzyl benzoate is an organic compound which is used as a medication and insect repellent. As a medication it is used to treat scabies and lice. For scabies either permethrin or malathion is typically preferred. It is applied to the skin as a lotion. Typically two to three applications are needed. It is also present in Balsam of Peru, Tolu balsam, and in a number of flowers.

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

Octyl acetate, or octyl ethanoate, is an organic compound with the formula CH3(CH2)7O2CCH3. It is classified as an ester that is formed from 1-octanol (octyl alcohol) and acetic acid. It is found in oranges, grapefruits, and other citrus products.

<span class="mw-page-title-main">Phenylpropanoid</span>

The phenylpropanoids are a diverse family of organic compounds that are synthesized by plants from the amino acids phenylalanine and tyrosine. Their name is derived from the six-carbon, aromatic phenyl group and the three-carbon propene tail of coumaric acid, which is the central intermediate in phenylpropanoid biosynthesis. From 4-coumaroyl-CoA emanates the biosynthesis of myriad natural products including lignols, flavonoids, isoflavonoids, coumarins, aurones, stilbenes, catechin, and phenylpropanoids. The coumaroyl component is produced from cinnamic acid.

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

2-Ethylhexanol (abbreviated 2-EH) is an organic compound with formula C8H18O. It is a branched, eight-carbon chiral alcohol. It is a colorless liquid that is poorly soluble in water but soluble in most organic solvents. It is produced on a large scale (>2,000,000,000 kg/y) for use in numerous applications such as solvents, flavors, and fragrances and especially as a precursor for production of other chemicals such as emollients and plasticizers. It is encountered in plants, fruits, and wines. The odor has been reported as "heavy, earthy, and slightly floral" for the R enantiomer and "a light, sweet floral fragrance" for the S enantiomer.

<span class="mw-page-title-main">4-Methylcyclohexanemethanol</span> Chemical compound

4-Methylcyclohexanemethanol (MCHM, systematic name 4-methylcyclohexylmethanol) is an organic compound with the formula CH3C6H10CH2OH. Classified as a saturated higher alicyclic primary alcohol. Both cis and trans isomers exist, depending on the relative positions of the methyl (CH3) and hydroxymethyl (CH2OH) groups on the cyclohexane ring. Commercial samples of MCHM consists of a mixture of these isomers as well as other components that vary with the supplier.

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

Benzyl cinnamate is the chemical compound which is the ester derived from cinnamic acid and benzyl alcohol.

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

Cinnamyl acetate is a chemical compound of the cinnamyl ester family, in which the variable R group is substituted by a methyl group. As a result of the non-aromatic carbon-carbon double bond, cinnamyl acetate can exist in a Z and an E configuration:

References

  1. Steffen Arctander: Perfume and Flavor Chemicals. ISBN   0-931710-37-5
  2. "Benzyl salicylate". The Good Scents Company.
  3. Belsito, D; Bickers, D; Bruze, M; Calow, P; Greim, H; Hanifin, JM; Rogers, AE; Saurat, JH; Sipes, IG; Tagami, H (2007). "Toxicologic and Dermatologic Assessments for Three Groups of Fragrance Ingredients: 1) Related Esters and Alcohols of Cinnamic Acid and Cinnamic Alcohol, 2) Ionones, 3) Salicylates" (PDF). Food and Chemical Toxicology. 45 (Supplement 1): S1-23. doi:10.1016/j.fct.2007.09.087. PMID   18035463. Archived from the original (PDF) on 2021-01-12. Retrieved 2012-04-05.
  4. "Standards Restricted". International Fragrance Association. Archived from the original on 2012-01-04.
  5. An Introduction to Perfumery by Curtis & Williams 2nd Edition, 2009, ISBN   978-0-9608752-8-3, ISBN   978-1-870228-24-4