Cannabis Compound Database: Showing Compound Card for Decanal (CDB000588)

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Record Information

Version

1.0

Created at

2020-03-19 00:45:19 UTC

Updated at

2020-12-07 19:07:33 UTC

CannabisDB ID

CDB000588

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

Decanal

Description

Decanal, also known as n-decyl aldehyde or caprinaldehyde, belongs to the class of organic compounds known as medium-chain aldehydes. These are an aldehyde with a chain length containing between 6 and 12 carbon atoms. Thus, decanal is considered to be a fatty aldehyde lipid molecule. Decanal is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Decanal is a sweet, aldehydic, and citrus tasting compound. Decanal is found, on average, in the highest concentration within a few different foods, such as corianders, dills, and gingers and in a lower concentration in limes, sweet oranges, and safflowers. Decanal has also been detected, but not quantified in, several different foods, such as fishes, cauliflowers, citrus, fats and oils, and lemon grass. This could make decanal a potential biomarker for the consumption of these foods. Decanal is a potentially toxic compound. Decanal, with regard to humans, has been found to be associated with several diseases such as uremia, asthma, and perillyl alcohol administration for cancer treatment; decanal has also been linked to the inborn metabolic disorder celiac disease. Decanal occurs naturally and is used in fragrances and flavoring. Chronic exposure of uremic toxins can lead to a number of conditions including renal damage, chronic kidney disease and cardiovascular disease. Uremic toxins tend to accumulate in the blood either through dietary excess or through poor filtration by the kidneys. Decanal is one of several aldehydes that are found in cannabis plants (PMID: 6991645 ). Decanal occurs naturally and is used in fragrances and flavoring. Decanal occurs in nature and is an important component in citrus along with octanal, citral, and sinensal. Decanal is also an important component of buckwheat odour.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1-Decanal	ChEBI
1-Decyl aldehyde	ChEBI
Capraldehyde	ChEBI
Caprinaldehyde	ChEBI
Decanaldehyde	ChEBI
N-Decaldehyde	ChEBI
N-Decanal	ChEBI
N-Decyl aldehyde	ChEBI
1-Decanal(mixed isomers)	HMDB
Aldehyde C10	HMDB
C-10 Aldehyde	HMDB
Capric aldehyde	HMDB
Caprinic aldehyde	HMDB
Decaldehyde	HMDB
Decanal (acd/name 4.0)	HMDB
Decyl aldehyde	HMDB
Decylic aldehyde	HMDB
N-Decanal (capric aldehyde)	HMDB
Decanal	MeSH

Chemical Formula

C₁₀H₂₀O

Average Molecular Weight

156.27

Monoisotopic Molecular Weight

156.1514

IUPAC Name

decanal

Traditional Name

decanal

CAS Registry Number

112-31-2

SMILES

CCCCCCCCCC=O

InChI Identifier

InChI=1S/C10H20O/c1-2-3-4-5-6-7-8-9-10-11/h10H,2-9H2,1H3

InChI Key

KSMVZQYAVGTKIV-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as medium-chain aldehydes. These are an aldehyde with a chain length containing between 6 and 12 carbon atoms.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Medium-chain aldehydes

Alternative Parents

Substituents

Medium-chain aldehyde
Alpha-hydrogen aldehyde
Organic oxide
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

fatty aldehyde (CHEBI:31457 )
Fatty aldehydes (C12307 )
Fatty aldehydes (LMFA06000052 )
a fatty aldehyde (CPD-8490 )

Ontology

Dermal

Enteral:

Ingestion

Source:

Biological:

Animal

Plant:

Poaceae

Biological location:

Subcellular:

Biofluid and excreta:

Role

Indirect biological role:

Uremic toxin

Industrial application:

Food and nutrition:

Flavoring agent

Personal care products:

Household products:

Antifungal

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	-5 °C	Not Available
Boiling Point	207 to 209 °C	Wikipedia
Water Solubility	Not Available	Not Available
logP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	4.44	ALOGPS
logP	3.43	ChemAxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	17.79	ChemAxon
pKa (Strongest Basic)	-6.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	17.07 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	48.55 m³·mol⁻¹	ChemAxon
Polarizability	20.66 Å³	ChemAxon
Number of Rings	0	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)	splash10-052f-9000000000-5c4742446d704137c4cd	2014-09-20	View Spectrum
GC-MS	Decanal, non-derivatized, GC-MS Spectrum	splash10-052f-9000000000-7749bc046eaf4c263d51	Spectrum
GC-MS	Decanal, non-derivatized, GC-MS Spectrum	splash10-052f-9000000000-87164b5c9889aeaf6447	Spectrum
GC-MS	Decanal, non-derivatized, GC-MS Spectrum	splash10-052f-9000000000-68c403b2d9fe194c1c55	Spectrum
GC-MS	Decanal, non-derivatized, GC-MS Spectrum	splash10-05mo-9100000000-d33aea8d64934a73baad	Spectrum
GC-MS	Decanal, non-derivatized, GC-MS Spectrum	splash10-052f-9000000000-7749bc046eaf4c263d51	Spectrum
GC-MS	Decanal, non-derivatized, GC-MS Spectrum	splash10-052f-9000000000-87164b5c9889aeaf6447	Spectrum
GC-MS	Decanal, non-derivatized, GC-MS Spectrum	splash10-052f-9000000000-68c403b2d9fe194c1c55	Spectrum
GC-MS	Decanal, non-derivatized, GC-MS Spectrum	splash10-05mo-9100000000-d33aea8d64934a73baad	Spectrum
Predicted GC-MS	Decanal, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-05g3-9100000000-74578afa9afd554784e5	Spectrum
Predicted GC-MS	Decanal, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Decanal, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positive	splash10-052f-9000000000-27a6eb7adbde8b4df4eb	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positive	splash10-052f-9000000000-6583e86a6ea49f801678	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (HP 5970) , Positive	splash10-052f-9000000000-68c403b2d9fe194c1c55	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positive	splash10-05mo-9100000000-d33aea8d64934a73baad	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-0a4i-6900000000-e1d9d4a1d621cdb8e783	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-1900000000-2364cb822acc74394aa5	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4r-8900000000-a60793d40772b1ee3917	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-9000000000-13163f941fae3335f3dc	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0900000000-f8919934fe6be4ffd0fa	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-2900000000-96f0e3848fdde9ff6026	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9100000000-3a8fd3c6c088c5e11ca6	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0900000000-f6034c6a8245c68a37ac	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-0900000000-e8b015c2539ebca0f921	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-05mo-9000000000-37e48635ff257cb68c23	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0aou-9000000000-1723af53a3cc3d7ba5d5	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4l-9000000000-e15457d7e27d24aee44b	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-9000000000-c777b63c4ee6c891865e	2021-09-23	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50.18 MHz, CDCl₃, experimental)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl₃, experimental)	Spectrum

Pathways

Not Available

Protein Targets

Enzymes

Protein Name	Gene Name	Locus	Uniprot ID	Details
Retinal dehydrogenase 2	ALDH1A2	15q21.3	O94788	details
Aldehyde dehydrogenase family 8 member A1	ALDH8A1	6q23.2	Q9H2A2	details

Transporters

Not Available

Metal Bindings

Not Available

Receptors

Protein Name	Gene Name	Locus	Uniprot ID	Details
Retinal dehydrogenase 2	ALDH1A2	15q21.3	O94788	details
Taste receptor type 1 member 3	TAS1R3	1p36.33	Q7RTX0	details
Taste receptor type 1 member 2	TAS1R2	1p36.13	Q8TE23	details

Transcriptional Factors

Not Available

Concentrations Data

Not Available

External Links

HMDB ID

HMDB0011623

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

Decanal

METLIN ID

Not Available

PubChem Compound

8175

PDB ID

Not Available

ChEBI ID

31457

References

General References

Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]

Enzymes

Enzyme Details

1. Retinal dehydrogenase 2

General function:: Involved in oxidoreductase activity
Specific function:: Recognizes as substrates free retinal and cellular retinol-binding protein-bound retinal. Does metabolize octanal and decanal but does not metabolize citral, benzaldehyde, acetaldehyde and propanal efficiently (By similarity).
Gene Name:: ALDH1A2
Uniprot ID:: O94788
Molecular weight:: 54672.24

Enzyme Details

2. Aldehyde dehydrogenase family 8 member A1

General function:: Involved in oxidoreductase activity
Specific function:: Converts 9-cis-retinal to 9-cis-retinoic acid. Has lower activity towards 13-cis-retinal. Has much lower activity towards all-trans-retinal. Has highest activity with benzaldehyde and decanal (in vitro). Has a preference for NAD, but shows considerable activity with NADP (in vitro)
Gene Name:: ALDH8A1
Uniprot ID:: Q9H2A2
Molecular weight:: 53400.9

Showing Compound Card for Decanal (CDB000588)

Structure for CDB000588 (Decanal)

Enzymes