Coniferyl alcohol

Coniferyl alcohol
Compound Structure:
Synonyms: CONIFERYL ALCOHOL;458-35-5;Coniferol;4-(3-hydroxyprop-1-en-1-yl)-2-methoxyphenol;32811-40-8;(E)-Coniferyl alcohol;trans-Coniferyl alcohol;gamma-Hydroxyisoeugenol;Coniferyl alcohol, E-
Compound ID: NMPC-387
PubChem ID:

1549095

Molecular Formula: C10H12O3
Canonical SMILES: COC1=C(C=CC(=C1)C=CCO)O
InChIKey: JMFRWRFFLBVWSI-NSCUHMNNSA-N
About the compound:

Coniferol, also recognized as coniferyl alcohol, falls within the phenylpropanoid category, embodying an organic compound with the formula C10H12O3. It exhibits a melting point between 74-80°C and a boiling point of 163-165°C under certain conditions, demonstrating its stability across varied temperature ranges [1,2]. This compound is integral to the production of lignin and lignans via the phenylpropanoid pathway, serving as a primary monolignol. Lignin, a vital structural component in plant cell walls, contributes to the strength of wood and stems. Coniferyl alcohol is involved in intricate biochemical pathways that lead to the creation of eugenol, stilbenoids, coumarins, and various esters present in natural resins such as gum benzoin. Its prevalence in both gymnosperms and angiosperms underscores its widespread importance in the plant world [2]. Furthermore, coniferyl alcohol is crucial in the biosynthesis of substances like (+)-pinoresinol, facilitated by specific plant proteins found in species like Forsythia intermedia and Arabidopsis thaliana. This selective synthesis highlights the variety of natural products derived from coniferol and its significance in plant biochemistry, including its potential in pheromone applications, notably in honey bee communication [2]. The detection of coniferol in a broad array of plants, such as Amaranthus hypochondriacus and Arabidopsis thaliana, underscores its essential function in plant metabolism and as a foundational element for complex natural products [1]. Its importance spans structural and functional roles, including as a pheromone and in volatile oils, emphasizing its biological relevance [3].

References 

1. "Coniferol | C10H12O3 | ChemSpider." Available at: https://www.chemspider.com/Chemical-Structure.1266063.html.

2. Coniferyl alcohol." Wikipedia, The Free Encyclopedia. Available at: https://en.wikipedia.org/wiki/Coniferyl_alcohol.

3. "Coniferol (CHEBI:17745)." ChEBI, The European Bioinformatics Institute. Available at: https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:17745.

GHS Hazard Statements

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]

H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

H335 (100%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]


Properties:

Chemical and Physical Properties

Property Name

Property Value

Molecular Weight

180.20 g/mol

XLogP3

1.4

Hydrogen Bond Donor Count

2

Hydrogen Bond Acceptor Count

3

Rotatable Bond Count

3

Exact Mass

180.078644241 g/mol

Monoisotopic Mass

180.078644241 g/mol

Topological Polar Surface Area

49.7²

Heavy Atom Count

13

Formal Charge

0

Complexity

168

Isotope Atom Count

0

Defined Atom Stereocenter Count

0

Undefined Atom Stereocenter Count

0

Defined Bond Stereocenter Count

1

Undefined Bond Stereocenter Count

0

Covalently-Bonded Unit Count

1

Compound Is Canonicalized

Yes

Physical Description

Solid; [Merck Index] White or yellow hygroscopic powder; [Alfa Aesar MSDS]

Meting Point

74 °C

Vapor Pressure

0.0000088 [mmHg]

Source: PubChem

Source Species: Artocarpus altilis.
Vernonia amygdalina
Vernonia blumeoides
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