8-Hexadecenal, 14-methyl-, (Z)-

8-Hexadecenal, 14-methyl-, (Z)-
Compound Structure:
Synonyms: (Z)-14-Methylhexadec-8-enal;(Z)-14-METHYL-8-HEXADECEN-1-AL;8-Hexadecenal, 14-methyl-, (Z)-;(z)-14-methyl-8-hexadecenal;14Z-Methyl-8-hexadecenal;14-Methyl-Z-8-Hexadecenal;14-Methyl (8Z)-hexadecenal
Compound ID: NMPC-501
PubChem ID:

5364688

Molecular Formula: C17H32O
Canonical SMILES: CCC(C)CCCCC=CCCCCCCC=O
InChIKey: HSGUJTMCFWXGAP-ALCCZGGFSA-N
About the compound:

Bornyl acetate is a chemical compound with the molecular formula C12H20O2 and a molecular weight of 196.29 g/mol. It is known as the acetate ester of borneol and is used in various applications, including as a food additive, flavoring agent, and odor agent. This compound is notable for its presence in the essential oils extracted from the needles of conifers in the Pinaceae family, primarily contributing to their distinctive odor[1]. The compound is found in both its (+) and (-) enantiomers in nature, each exhibiting unique properties and activities. Bornyl acetate's "piney" aroma is utilized in perfumes, air fresheners, cleaners, and personal care products. Additionally, it has been reported to possess anti-inflammatory, analgesic, antibiotic, and sedative properties, making it an active ingredient in certain over-the-counter cough and cold medications as recognized by the US Food and Drug Administration[2]. The chemical and physical properties of bornyl acetate have been thoroughly studied. It has a boiling point of 223.5°C at 760 mmHg and a density of approximately 1.0 g/cm³. Its flash point is recorded at 87.4°C, indicating the temperature at which it can vaporize to form an ignitable mixture in air. Bornyl acetate demonstrates moderate solubility in water, further indicating its potential for various biological and industrial applications[3]. Research on the (-)-enantiomer of bornyl acetate, available from TargetMol, reveals its potential in antifungal activities and as a cosmeceutical ingredient due to its whitening and antioxidant activities. It has been shown to downregulate proinflammatory cytokines and reduce inflammatory responses both in vitro and in vivo. This enantiomer has been isolated from hyssop oil and exhibits notable efficacy against powdery mildew infection in barley seedlings when applied alone[4].

Reference 

1. Wikipedia contributors. "Bornyl acetate." Wikipedia, https://en.wikipedia.org/wiki/Bornyl_acetate.

2. American Chemical Society. "Bornyl acetate - Molecule of the Week Archive." American Chemical Society, https://www.acs.org/molecule-of-the-week/archive/b/bornyl-acetate.html.

3. ChemSpider. "(+)-Bornyl acetate | C12H20O2." ChemSpider, https://www.chemspider.com/Chemical-Structure.5323220.html.

4. TargetMol. "(-)-Bornyl acetate | p38 MAPK | NF-κB | JNK | Antifungal." TargetMol, https://www.targetmol.com/compound/%28-%29-Bornyl%20acetate.

Properties:

Chemical and Physical Properties

Property Name

Property Value

Molecular Weight

252.4 g/mol

XLogP3-AA

6.4

Hydrogen Bond Donor Count

0

Hydrogen Bond Acceptor Count

1

Rotatable Bond Count

13

Exact Mass

252.245315640 g/mol

Monoisotopic Mass

252.245315640 g/mol

Topological Polar Surface Area

17.1Ų

Heavy Atom Count

18

Formal Charge

0

Complexity

196

Isotope Atom Count

0

Defined Atom Stereocenter Count

0

Undefined Atom Stereocenter Count

1

Defined Bond Stereocenter Count

1

Undefined Bond Stereocenter Count

0

Covalently-Bonded Unit Count

1

Compound Is Canonicalized

Yes

Source: PubChem       

Source Species: Tetracarpidium conophorum
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