Cannabis Compound Database: Showing Compound Card for Salicyladehyde (CDB000667)

Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Protein target Pathways Concentrations Links References XML

Record Information

Version

1.0

Created at

2020-03-19 00:50:02 UTC

Updated at

2020-12-07 19:07:39 UTC

CannabisDB ID

CDB000667

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

Salicyladehyde

Description

Salicyladehyde or 2-Hydroxybenzaldehyde, also known as salicylal or o-formylphenol, belongs to the class of organic compounds known as hydroxybenzaldehydes. These are organic aromatic compounds containing a benzene ring carrying an aldehyde group and a hydroxyl group. Salicylaldehyde is a colorless oily liquid. At high concentrations it has a bitter almond odor. In nature, salicylaldehyde has been identified as the metabolite responsible for the characteristic aroma of buckwheat (PMID: 26003350 ). It is also a component of castoreum, used in perfumery (PMID: 24249178 ). The defensive secretions of some leaf beatle species, such as the red poplar leaf beetle, also contain salicylaldehyde (PMID: 27033853 ). It has also been detected in the volatile fraction of Cannabis sativa samples (PMID: 26657499 ). Salicyladehyde is also a constituent of cannabis smoke and is volatilized during the combustion of cannabis ( Ref:DOI ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
O-Formylphenol	ChEBI
O-Hydroxybenzaldehyde	ChEBI
Salicylal	ChEBI
Salicylaldehyd	ChEBI
Salizylaldehyd	ChEBI
2-Formylphenol	HMDB
FEMA 3004	HMDB
Salicylaldehyde, 8ci	HMDB
Salicylic aldehyde	HMDB
2-Hydroxybenzaldehyde	ChEBI
Salicylaldehyde ester	MeSH
2-Hydroxy-1-benzaldehyde	HMDB
Salicylaldehyde	HMDB

Chemical Formula

C₇H₆O₂

Average Molecular Weight

122.12

Monoisotopic Molecular Weight

122.0368

IUPAC Name

2-hydroxybenzaldehyde

Traditional Name

salicylaldehyde

CAS Registry Number

90-02-8

SMILES

OC1=CC=CC=C1C=O

InChI Identifier

InChI=1S/C7H6O2/c8-5-6-3-1-2-4-7(6)9/h1-5,9H

InChI Key

SMQUZDBALVYZAC-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydroxybenzaldehydes. These are organic aromatic compounds containing a benzene ring carrying an aldehyde group and a hydroxyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Hydroxybenzaldehydes

Alternative Parents

Substituents

Hydroxybenzaldehyde
Benzoyl
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Benzenoid
Monocyclic benzene moiety
Vinylogous acid
Organic oxide
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

hydroxybenzaldehyde (CHEBI:16008 )
a small molecule (SALICYLALDEHYDE )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Food

Biological:

Plant:

Poaceae

Biological location:

Biofluid and excreta:

Feces

Subcellular:

Cytoplasm

Cell and elements:

Extracellular

Role

Industrial application:

Personal care products:

Perfuming agent

Household products:

Pesticide:

Insect repellent

Food and nutrition:

Flavoring agent

Biological role:

Nutrient

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	0.7 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	17 mg/mL at 86 °C	Not Available
logP	1.81	Not Available

Predicted Properties

Property	Value	Source
logP	1.22	ALOGPS
logP	2.03	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Acidic)	8.4	ChemAxon
pKa (Strongest Basic)	-6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	34.62 m³·mol⁻¹	ChemAxon
Polarizability	11.89 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-00di-9600000000-af7c15a0b15606c87955	2014-09-20	View Spectrum
GC-MS	Salicyladehyde, non-derivatized, GC-MS Spectrum	splash10-00di-8900000000-583bbd8c5848ff6c26b1	Spectrum
GC-MS	Salicyladehyde, non-derivatized, GC-MS Spectrum	splash10-00di-9800000000-e0a9ad2626c3dba695db	Spectrum
GC-MS	Salicyladehyde, non-derivatized, GC-MS Spectrum	splash10-00dr-9500000000-e18d8d6fc6476767e239	Spectrum
GC-MS	Salicyladehyde, non-derivatized, GC-MS Spectrum	splash10-00kf-3900000000-632e662634ab33df04b6	Spectrum
GC-MS	Salicyladehyde, non-derivatized, GC-MS Spectrum	splash10-00di-8900000000-583bbd8c5848ff6c26b1	Spectrum
GC-MS	Salicyladehyde, non-derivatized, GC-MS Spectrum	splash10-00di-9800000000-e0a9ad2626c3dba695db	Spectrum
GC-MS	Salicyladehyde, non-derivatized, GC-MS Spectrum	splash10-00dr-9500000000-e18d8d6fc6476767e239	Spectrum
GC-MS	Salicyladehyde, non-derivatized, GC-MS Spectrum	splash10-00kf-3900000000-632e662634ab33df04b6	Spectrum
Predicted GC-MS	Salicyladehyde, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00di-6900000000-f3f3aaf417e6320169c2	Spectrum
Predicted GC-MS	Salicyladehyde, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00di-9700000000-ad6e9da1650fde48af74	Spectrum
Predicted GC-MS	Salicyladehyde, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Salicyladehyde, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , negative	splash10-00di-0900000000-be0f193ffc0b577e05b8	2020-07-21	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QTOF 35V, negative	splash10-00di-0900000000-f6bbf793b513247a43f9	2020-07-21	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 0V, positive	splash10-00di-0900000000-1fd6de1de02ee87b504b	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 0V, positive	splash10-00di-0900000000-ee44a10727fab869a4d2	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 0V, positive	splash10-00di-0900000000-690d3ae60cf893b9ff06	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 0V, positive	splash10-00di-0900000000-d8a2c0fadb6a182d8f0a	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 1V, positive	splash10-00di-2900000000-97030dc87c10651e96a2	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 2V, positive	splash10-00dj-5900000000-8d437ad0fdcd47cd7bcb	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 2V, positive	splash10-006t-9600000000-f45ab5984169c5818bcb	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - 35V, Negative	splash10-00di-0900000000-71123584d3741c4699ab	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0900000000-1255ecd1c31ba1344679	2016-06-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-2900000000-a6ed64aa8049a5f6c188	2016-06-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udi-9000000000-a9b45cf42b4fda665c1d	2016-06-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0900000000-028de9906ead3d0f2c4f	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-0900000000-de8eee3eed47a07dd7d8	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0fxx-9100000000-8365be7aef3c22b70d98	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-05fs-3900000000-5b3e0b81e8c054ff2cf6	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0cdj-9400000000-9a54f9d98b585a8691d9	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udi-9000000000-23bd778d9581ae5a1f0d	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-4900000000-f0356154a12f6010da9e	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-9000000000-d0111d930d0fb38e1292	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-00kf-9000000000-f94ec230876fa6f26623	2021-09-22	View Spectrum

NMR

Type	Description	View
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, CDCl₃, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, benzene, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, benzene, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum

Pathways

Not Available

Protein Targets

Enzymes

Not Available

Transporters

Not Available

Metal Bindings

Not Available

Receptors

Not Available

Transcriptional Factors

Not Available

Concentrations Data

Not Available

External Links

HMDB ID

HMDB0034170

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Salicylaldehyde

METLIN ID

Not Available

PubChem Compound

6998

PDB ID

ChEBI ID

16008

References

General References

Janes D, Kreft S: Salicylaldehyde is a characteristic aroma component of buckwheat groats. Food Chem. 2008 Jul 15;109(2):293-8. doi: 10.1016/j.foodchem.2007.12.032. Epub 2008 Feb 5. [PubMed:26003350 ]
Tang R, Webster FX, Muller-Schwarze D: Phenolic compounds from male castoreum of the North American beaver,Castor canadensis. J Chem Ecol. 1993 Jul;19(7):1491-500. doi: 10.1007/BF00984892. [PubMed:24249178 ]
Pauls G, Becker T, Rahfeld P, Gretscher RR, Paetz C, Pasteels J, von Reuss SH, Burse A, Boland W: Two Defensive Lines in Juvenile Leaf Beetles; Esters of 3-nitropropionic Acid in the Hemolymph and Aposematic Warning. J Chem Ecol. 2016 Mar;42(3):240-8. doi: 10.1007/s10886-016-0684-0. Epub 2016 Mar 31. [PubMed:27033853 ]
Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. [PubMed:26657499 ]

Showing Compound Card for Salicyladehyde (CDB000667)

Structure for CDB000667 (Salicyladehyde)