Cannabis Compound Database: Showing Compound Card for Hexanal (CDB000057)

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Identification Taxonomy Ontology Physical properties Spectra Protein target Pathways Concentrations Links References transporters (1) Show 4 proteins XML

Record Information

Version

1.0

Created at

2020-03-18 23:23:11 UTC

Updated at

2020-12-07 19:07:01 UTC

CannabisDB ID

CDB000057

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

Hexanal

Description

Hexanal, 1-hexanal, n-hexanal, is also known as caproaldehyde or hexanaldehyde. It belongs to the class of organic compounds known as medium-chain aldehydes which have a chain length between 6 and 12 carbon atoms and therefore is considered a fatty aldehyde lipid molecule. Hexanal is a very hydrophobic molecule that is relatively neutral. It is a colorless clear liquid. It has a fresh green, fatty or grassy scent with a green, fatty, leafy or aldehydic taste. Hexanal exists in all eukaryotes, from yeast to humans. Hexanal is found in cannabis plants (PMID: 6991645 ). Different foods contain hexanal with the highest concentrations found in black walnuts, corns, and tea and with lower concentrations in common grapes, thornless blackberries, and tortilla. Hexanal has also been detected in palms, mentha (mint), wax gourds, grapes, and kiwis making hexanal a potential biomarker for the consumption of these foods. Hexanal has been used to increase post-harvest longevity and color of certain fruits ( Ref:DOI ). Hexanal was also detected in humans breastmilk samples. Among mediators of oxidative stress, highly reactive secondary aldehydic lipid peroxidation products can initiate the processes of spontaneous mutagenesis and carcinogenesis and can also act as a growth-regulating factors and signaling molecules. In specimens obtained from adult patients with brain astrocytomas, lower levels of n-hexanal, together with higher levels of 2-hydroxyhexanal and 4-hydroxynonena, are associated with poorer patient prognosis (PMID: 17487452 ). Hexanal has also been identified as a uremic toxin according to the European Uremic Toxin Working Group because its concentrations in uremic patients were found to exceed the normal general population concentrations (PMID: 22626821 ). Hexanal is a volatile compound that has been associated with the development of undesirable flavours and has been proposed as a potential marker of milk quality. Hexanal, a major breakdown product of linoleic acid (LA, n ‚Äì 6, an polyunsaturated fatty acid, PUFA) oxidation, has been used to follow the course of lipid oxidation and off-flavour development in foods. A "cardboard-like" off-flavour is frequently associated with dehydrated milk products such as baby formulae and was correlated with the hexanal concentration ( Ref:DOI ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
1-Hexanal	ChEBI
Aldehyde C-6	ChEBI
C6 Aldehyde	ChEBI
Caproaldehyde	ChEBI
Caproic aldehyde	ChEBI
Hexaldehyde	ChEBI
Hexan-1-al	ChEBI
Hexanaldehyde	ChEBI
Hexoic aldehyde	ChEBI
Hexylaldehyde	ChEBI
N-C5H11CHO	ChEBI
N-Caproaldehyde	ChEBI
N-Caproic aldehyde	ChEBI
N-Hexanal	ChEBI
N-Hexylaldehyde	ChEBI
Capronaldehyde	HMDB
Hexanal	MeSH
n-Capronaldehyde	HMDB

Chemical Formula

C₆H₁₂O

Average Molecular Weight

100.16

Monoisotopic Molecular Weight

100.0888

IUPAC Name

hexanal

Traditional Name

hexanal

CAS Registry Number

66-25-1

SMILES

CCCCCC=O

InChI Identifier

InChI=1S/C6H12O/c1-2-3-4-5-6-7/h6H,2-5H2,1H3

InChI Key

JARKCYVAAOWBJS-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 aldehydes (LMFA06000109 )
an <i>n</i>-alkanal (HEXANAL )

Ontology

Dermal

Enteral:

Ingestion

Biological location:

Biofluid and excreta:

Source:

Biological:

Animal

Plant:

Role

Industrial application:

Food and nutrition

Indirect biological role:

Uremic toxin

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	-56 °C	Not Available
Boiling Point	130 - 131 °C	Wikipedia
Water Solubility	5.64 mg/mL at 30 °C	Not Available
logP	1.78	HANSCH,C ET AL. (1995)

Predicted Properties

Property	Value	Source
logP	2.37	ALOGPS
logP	1.65	ChemAxon
logS	-1.4	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	4	ChemAxon
Refractivity	30.15 m³·mol⁻¹	ChemAxon
Polarizability	12.32 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-9000000000-72ae5d9e7cc61abeff7f	2014-09-20	View Spectrum
GC-MS	Hexanal, non-derivatized, GC-MS Spectrum	splash10-0006-9000000000-65f52440a5d20229be6c	Spectrum
GC-MS	Hexanal, non-derivatized, GC-MS Spectrum	splash10-052f-9000000000-89f4d5edf8639a778ef4	Spectrum
GC-MS	Hexanal, non-derivatized, GC-MS Spectrum	splash10-052f-9000000000-98fd24ab2b6d3d9cf3cf	Spectrum
GC-MS	Hexanal, non-derivatized, GC-MS Spectrum	splash10-0006-9000000000-65f52440a5d20229be6c	Spectrum
GC-MS	Hexanal, non-derivatized, GC-MS Spectrum	splash10-052f-9000000000-89f4d5edf8639a778ef4	Spectrum
GC-MS	Hexanal, non-derivatized, GC-MS Spectrum	splash10-052f-9000000000-98fd24ab2b6d3d9cf3cf	Spectrum
Predicted GC-MS	Hexanal, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-004l-9000000000-f6f6f2d2922256923f62	Spectrum
Predicted GC-MS	Hexanal, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)	splash10-0089-9200000000-a864c6ae8f499374570f	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)	splash10-00lr-9000000000-c35aa664e0abaa7ff754	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)	splash10-00lr-9100000000-32a2d24a74c86ead890b	2012-07-25	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positive	splash10-0006-9000000000-65f52440a5d20229be6c	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positive	splash10-052f-9000000000-13ae9f72ffb8573eac28	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - EI-B (HITACHI RMU-6M) , Positive	splash10-052f-9000000000-e06f68e7ce93f5ced938	2012-08-31	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0udi-4900000000-3680e8fedab54e7572cb	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0ue9-9400000000-d3150dfd70fdee4bfc78	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-9000000000-c161db43b692fc558533	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-9000000000-16f962506c9316343166	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0002-9000000000-1fd34894f517ecf1f19a	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-054aa18a9a05fa35cf01	2015-05-27	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-9000000000-658fe53778817eb82301	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-9000000000-b0e3f2f55178b8aacda1	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-c5c7ace495de00bff008	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a5c-9000000000-d214e2877cddafdcb757	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-052f-9000000000-f2f5a7e46a17ef9b2c6b	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4l-9000000000-7d79b3949754c5802624	2021-09-23	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, CDCl₃, 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, 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
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, experimental)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl₃, experimental)	Spectrum

Pathways

Not Available

Protein Targets

Enzymes

Not Available

Transporters

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

Metal Bindings

Protein Name	Gene Name	Locus	Uniprot ID	Details
Cholesterol side-chain cleavage enzyme, mitochondrial	CYP11A1	15q23-q24	P05108	details

Receptors

Protein Name	Gene Name	Locus	Uniprot ID	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

HMDB0005994

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

Hexanal

METLIN ID

Not Available

PubChem Compound

6184

PDB ID

Not Available

ChEBI ID

88528

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 ]
Duranton F, Cohen G, De Smet R, Rodriguez M, Jankowski J, Vanholder R, Argiles A: Normal and pathologic concentrations of uremic toxins. J Am Soc Nephrol. 2012 Jul;23(7):1258-70. doi: 10.1681/ASN.2011121175. Epub 2012 May 24. [PubMed:22626821 ]
Zajdel A, Wilczok A, Slowinski J, Orchel J, Mazurek U: Aldehydic lipid peroxidation products in human brain astrocytomas. J Neurooncol. 2007 Sep;84(2):167-73. doi: 10.1007/s11060-007-9367-6. Epub 2007 May 9. [PubMed:17487452 ]

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 Hexanal (CDB000057)

Structure for CDB000057 (Hexanal)

Transporters