Pinoresinol

Pinoresinol
Compound Structure:
Synonyms: Pinoresinol ;(+)-Pinoresinol ;487-36-5 ;D-PINORESINOL
Compound ID: NMPC-1416
PubChem ID:

73399

Molecular Formula: C20H22O6
Canonical SMILES: COC1=C(C=CC(=C1)C2C3COC(C3CO2)C4=CC(=C(C=C4)O)OC)O
InChIKey: HGXBRUKMWQGOIE-AFHBHXEDSA-N
About the compound:

Pinoresinol, a tetrahydrofuranlignan, is a natural compound found in various plant species and even in certain insects. It is present in Styrax species, Forsythia suspensa, and Forsythia koreana. Beyond these plants, pinoresinol has a fascinating occurrence in the caterpillar of the cabbage butterfly, Pierisrapae, where it functions as a defense mechanism against ants. In the human diet, pinoresinol can be found in several food sources. It is present in sesame seeds, Brassica vegetables (such as broccoli, Brussels sprouts, and cabbage), and olive oil. This diversity of sources indicates that pinoresinol is a relatively common component in various dietary items. Pinoresinol also demonstrates biological activity as it has been found toxic to larvae of the milkweed bug Oncopeltusfasciatus and to the haematophagous insect Rhodniusprolixus, which is known as a vector for Chagas disease. This suggests that pinoresinol could potentially have applications or implications in pest control or in the study of natural insect repellents. However, the current methods for isolating pinoresinol from plants are not highly efficient and yield low quantities of the compound. This limitation suggests a need for improved extraction techniques or synthesis methods to better utilize pinoresinol for research and potential practical applications.

Properties:

Chemical and Physical Properties

Property Name

Property Value

Molecular Weight

358.4 g/mol

XLogP3-AA

2.3

Hydrogen Bond Donor Count

2

Hydrogen Bond Acceptor Count

6

Rotatable Bond Count

4

Exact Mass

358.14163842 g/mol

Monoisotopic Mass

358.14163842 g/mol

Topological Polar Surface Area

77.4Ų

Heavy Atom Count

26

Formal Charge

0

Complexity

431

Isotope Atom Count

0

Defined Atom Stereocenter Count

4

Undefined Atom Stereocenter Count

0

Defined Bond Stereocenter Count

0

Undefined Bond Stereocenter Count

0

Covalently-Bonded Unit Count

1

Compound Is Canonicalized

Yes

Source: PubChem                        

Source Species: Landolphia owariensis
Luffa cylindrica
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