Cannabis Compound Database: Showing Compound Card for Caprylaldehyde (CDB000172)

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Identification Taxonomy Ontology Physical properties Spectra Protein target Pathways Concentrations Links References enzymes (1)transporters (1) Show 5 proteins XML

Record Information

Version

1.0

Created at

2020-03-18 23:27:27 UTC

Updated at

2020-12-07 19:07:12 UTC

CannabisDB ID

CDB000172

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

Caprylaldehyde

Description

Caprylaldehyde also known as Octanal, or aldehyde C8, belongs to the class of organic compounds known as medium-chain aldehydes, which are aldehydes with a chain length between 6 and 12 carbon atoms. Octanal is a fatty aldehyde lipid molecule. It is produced by¬†hydroformylation¬†of¬†heptene¬†and the¬†dehydrogenation¬†of¬†1-octanol ( ¬†doi:10.1002/14356007.a01_321.pub2 ). Caprylaldehyde is very hydrophobic, practically insoluble in water, and relatively neutral. Octanal is colorless or lightly yellow tinged fragrant liquid with a fruit-like (green, orange, rose, coconut) odor and a waxy, citrus or fruity taste. It occurs naturally in citrus (such as blood orange, lime, mandarin, orange) and other oils from bergamot, blood orange, lime, lemon, grapefruit, orange peel and yuzu peel. Caprylaldehyde is one of the simple aldehydes found in cannabis plants (PMID:6991645 ) as well as carrot root, celery shoot and leaf, ceylon cinnamon leaf, rose and witch hazel leaf ( Ref:DOI ). It is used commercially as a component in perfumes and in flavor production for the food industry. It is also used as a raw material for surfactants, for conditioners, for disinfectants and for plasticizers. It is used as an oil base for lubricants of synthetic resin and for emulsifiers of emulsion polymerization. Octanal is also used as a material for creams and ointments. Additionally, octanal is used as a masking agent, a perfuming agent and a viscosity controlling agent in the food and cosmetic industry.

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
1-Caprylaldehyde	ChEBI
1-Octaldehyde	ChEBI
1-Octanal	ChEBI
1-Octylaldehyde	ChEBI
Aldehyde C-8	ChEBI
C-8 Aldehyde	ChEBI
Caprylaldehyd	ChEBI
Caprylaldehyde	ChEBI
Caprylic aldehyde	ChEBI
Kaprylaldehyd	ChEBI
N-Caprylaldehyde	ChEBI
N-Octaldehyde	ChEBI
N-Octanal	ChEBI
N-Octyl aldehyde	ChEBI
N-Octylal	ChEBI
Octan-1-al	ChEBI
Octanaldehyde	ChEBI
Octanoic aldehyde	ChEBI
Octylaldehyd	ChEBI
Octylaldehyde	ChEBI
Oktanal	ChEBI
Oktylaldehyd	ChEBI
Aldehyde C8	HMDB
Antifoam-LF	HMDB
Octaldehyde	HMDB
Octanal	MeSH

Chemical Formula

C₈H₁₆O

Average Molecular Weight

128.21

Monoisotopic Molecular Weight

128.1201

IUPAC Name

octanal

Traditional Name

octanal

CAS Registry Number

124-13-0

SMILES

CCCCCCCC=O

InChI Identifier

InChI=1S/C8H16O/c1-2-3-4-5-6-7-8-9/h8H,2-7H2,1H3

InChI Key

NUJGJRNETVAIRJ-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:17935 )
Fatty aldehydes (C01545 )
Fatty aldehydes (LMFA06000028 )
an <i>n</i>-alkanal (CPD-371 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Animal

Plant:

Biological location:

Subcellular:

Biofluid and excreta:

Role

Industrial application:

Personal care products:

Perfuming agent

Household products:

Antimicrobial agent:

Disinfectant

Food and nutrition:

Flavoring agent

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	-23 °C	Not Available
Boiling Point	171 °C	Wikipedia
Water Solubility	0.56 mg/mL	Not Available
logP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	3.19	ALOGPS
logP	2.54	ChemAxon
logS	-2.6	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	6	ChemAxon
Refractivity	39.35 m³·mol⁻¹	ChemAxon
Polarizability	16.45 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-9000000000-23d54ae7b45c372a7325	2015-03-01	View Spectrum
GC-MS	Caprylaldehyde, non-derivatized, GC-MS Spectrum	splash10-052f-9000000000-fe177a98511039e9f7a6	Spectrum
GC-MS	Caprylaldehyde, non-derivatized, GC-MS Spectrum	splash10-052f-9000000000-5116ccc02f51ccb0e86a	Spectrum
GC-MS	Caprylaldehyde, non-derivatized, GC-MS Spectrum	splash10-052f-9000000000-b395bc62397f2d3ead7d	Spectrum
GC-MS	Caprylaldehyde, non-derivatized, GC-MS Spectrum	splash10-000x-9000000000-70ec440a61fb95915131	Spectrum
GC-MS	Caprylaldehyde, non-derivatized, GC-MS Spectrum	splash10-000i-9200000000-f67b980d2d2a991b2179	Spectrum
GC-MS	Caprylaldehyde, non-derivatized, GC-MS Spectrum	splash10-000i-9300000000-2f4aa9d5b7cd47e5d002	Spectrum
GC-MS	Caprylaldehyde, non-derivatized, GC-MS Spectrum	splash10-0udi-4970000000-957d3c05049cd98e4df4	Spectrum
GC-MS	Caprylaldehyde, non-derivatized, GC-MS Spectrum	splash10-052f-9000000000-fe177a98511039e9f7a6	Spectrum
GC-MS	Caprylaldehyde, non-derivatized, GC-MS Spectrum	splash10-052f-9000000000-5116ccc02f51ccb0e86a	Spectrum
GC-MS	Caprylaldehyde, non-derivatized, GC-MS Spectrum	splash10-052f-9000000000-b395bc62397f2d3ead7d	Spectrum
GC-MS	Caprylaldehyde, non-derivatized, GC-MS Spectrum	splash10-000x-9000000000-70ec440a61fb95915131	Spectrum
GC-MS	Caprylaldehyde, non-derivatized, GC-MS Spectrum	splash10-000i-9200000000-f67b980d2d2a991b2179	Spectrum
GC-MS	Caprylaldehyde, non-derivatized, GC-MS Spectrum	splash10-000i-9300000000-2f4aa9d5b7cd47e5d002	Spectrum
GC-MS	Caprylaldehyde, non-derivatized, GC-MS Spectrum	splash10-0udi-4970000000-957d3c05049cd98e4df4	Spectrum
Predicted GC-MS	Caprylaldehyde, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0adl-9000000000-e3eb771931f18e535c7b	Spectrum
Predicted GC-MS	Caprylaldehyde, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Caprylaldehyde, 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-afbedb8b18342773ec25	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positive	splash10-052f-9000000000-5116ccc02f51ccb0e86a	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (HP 5970) , Positive	splash10-052f-9000000000-e20fdcbb6710ee07f303	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positive	splash10-000x-9000000000-70ec440a61fb95915131	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-03di-5900000000-bfe65c70c387eb909dfe	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-004i-1900000000-e4de633fb7345cb25ac3	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-01t9-9600000000-ffa4810bd6f0997adbe2	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-9000000000-0663d075e83465e0b94a	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0900000000-54dee15774147b509eee	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-3900000000-0c41e22b27b06ecc562d	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-7cb58e4c39970a374f81	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004i-0900000000-e8448bc978ba2df6edde	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-004i-2900000000-6d2914c732c6d3bc363a	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-05mo-9000000000-e50228b21fdc354e7b1e	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4l-9000000000-834db11e54f8e63184e9	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4l-9000000000-35e82065f007831a2582	2021-09-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-9000000000-2e7e4295287c08d9ab42	2021-09-25	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 90 MHz, CDCl₃, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, CDCl₃, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, methanol, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, methanol, experimental)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Spectrum

Pathways

Not Available

Protein Targets

Enzymes

Protein Name	Gene Name	Locus	Uniprot ID	Details
Retinal dehydrogenase 2	ALDH1A2	15q21.3	O94788	details

Transporters

Protein Name	Gene Name	Locus	Uniprot ID	Details
Platelet glycoprotein 4	CD36	7q11.2	P16671	details

Metal Bindings

Not Available

Receptors

Protein Name	Gene Name	Locus	Uniprot ID	Details
Retinal dehydrogenase 2	ALDH1A2	15q21.3	O94788	details
Free fatty acid receptor 1	FFAR1	19q13.1	O14842	details
Free fatty acid receptor 4	FFAR4	10q23.33	Q5NUL3	details

Transcriptional Factors

Not Available

Concentrations Data

Not Available

External Links

HMDB ID

HMDB0001140

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

Octanal

METLIN ID

6033

PubChem Compound

454

PDB ID

Not Available

ChEBI ID

17935

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

Transporters

Enzyme Details

1. Platelet glycoprotein 4

General function:: Not Available
Specific function:: Seems to have numerous potential physiological functions. Binds to collagen, thrombospondin, anionic phospholipids and oxidized LDL. May function as a cell adhesion molecule. Directly mediates cytoadherence of Plasmodium falciparum parasitized erythrocytes. Binds long chain fatty acids and may function in the transport and/or as a regulator of fatty acid transport
Gene Name:: CD36
Uniprot ID:: P16671
Molecular weight:: 53054.0

Showing Compound Card for Caprylaldehyde (CDB000172)

Structure for CDB000172 (Caprylaldehyde)

Enzymes

Transporters