Cannabis Compound Database: Showing Compound Card for Heptanal (CDB000072)

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Record Information

Version

1.0

Created at

2020-03-18 23:23:44 UTC

Updated at

2020-12-07 19:07:03 UTC

CannabisDB ID

CDB000072

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

Heptanal

Description

Heptanal, also known as enanthal or N-heptaldehyde, 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, heptanal is a fatty aldehyde lipid molecule. It is an endogenous aldehyde resulting from membrane lipid oxidation. Heptanal is a flammable, slightly volatile colorless liquid of pervasive fruity to oily-greasy odor with an aldehydic, citrus, and fat taste. It is miscible with alcohols and practically insoluble in water. Heptanal is very hydrophobic and is relatively neutral. Heptanal exists in all eukaryotes, from yeast to humans. It is found in highest concentrations in corns, tea, and sweet oranges and in a lower concentrations in lemons, wild carrots, and carrots. Heptanal was detected in horned melons, common beets, dills, red bell peppers, and malus (crab apple) making it a potential biomarker for the consumption of these foods. Heptanal was distilled from castor oil and first described in 1878 ( Ref:DOI ). Heptanal naturally occurs in the essential oils of ylang-ylang (Cananga odorata), clary sage (Salvia sclarea), lemon (Citrus x limon), bitter orange (Citrus x aurantium), rose (Rosa) and hyacinth (Hyacinthus) ( Ref:DOI ). ¬†Heptanal is a simple aldehyde found in cannabis plants (PMID: 6991645 ). Because of heptanal‚Äôs strong fruity odor, it is used as precursor to components in perfumes and lubricants ( Ref:DOI ). For example, heptanal reacts with benzaldehyde in a Knoevenagel reaction under basic catalysis with high yield and selectivity (> 90%) to alpha-pentylcinnamaldehyde, which is also called jasmine aldehyde (because of the typical jasmine odor). This jasmine aldehyde has been used in fragrances. Heptanal may be a potential biomarker of lung cancer as it was found in the blood of lung cancer patients (PMID:28366212 ).

Structure

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

Synonyms

Value	Source
Aldehyde C-7	ChEBI
Enanthal	ChEBI
Enanthaldehyde	ChEBI
Enanthic aldehyde	ChEBI
Heptaldehyde	ChEBI
Heptanaldehyde	ChEBI
Heptyl aldehyde	ChEBI
Heptylaldehyde	ChEBI
N-C6H13CHO	ChEBI
N-Heptaldehyde	ChEBI
N-Heptanal	ChEBI
N-Heptylaldehyde	ChEBI
Oenanthal	ChEBI
Oenanthaldehyde	ChEBI
Oenanthic aldehyde	ChEBI
Oenanthol	ChEBI
1-Heptaldehyde	HMDB
1-Heptanal	HMDB
Aldehyde C7	HMDB
Enanthole	HMDB
FEMA 2540	HMDB
Heptan-1-al	HMDB
Oenanthole	HMDB
Heptanal	MeSH

Chemical Formula

C₇H₁₄O

Average Molecular Weight

114.19

Monoisotopic Molecular Weight

114.1045

IUPAC Name

heptanal

Traditional Name

heptanal

CAS Registry Number

111-71-7

SMILES

CCCCCCC=O

InChI Identifier

InChI=1S/C7H14O/c1-2-3-4-5-6-7-8/h7H,2-6H2,1H3

InChI Key

FXHGMKSSBGDXIY-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:34787 )
Fatty aldehydes (LMFA06000001 )
an <i>n</i>-alkanal (CPD-7620 )

Ontology

Dermal

Enteral:

Ingestion

Source:

Biological:

Animal

Plant:

Biological location:

Subcellular:

Biofluid and excreta:

Role

Industrial application:

Personal care products:

Perfuming agent

Food and nutrition:

Flavoring agent

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	-43.3 °C	Not Available
Boiling Point	152.8 °C	Wikipedia
Water Solubility	1.25 mg/mL at 25 °C	Not Available
logP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	2.59	ALOGPS
logP	2.1	ChemAxon
logS	-1.9	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	5	ChemAxon
Refractivity	34.75 m³·mol⁻¹	ChemAxon
Polarizability	14.4 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)	splash10-0006-9000000000-781fd8622d3cd4023d6f	2014-09-20	View Spectrum
GC-MS	Heptanal, non-derivatized, GC-MS Spectrum	splash10-0006-9000000000-183283cb2427145b7678	Spectrum
GC-MS	Heptanal, non-derivatized, GC-MS Spectrum	splash10-0006-9000000000-aedf02ade0aa5bd82d71	Spectrum
GC-MS	Heptanal, non-derivatized, GC-MS Spectrum	splash10-0006-9000000000-a85809c1e2c6b7471781	Spectrum
GC-MS	Heptanal, non-derivatized, GC-MS Spectrum	splash10-006x-9000000000-d026c39b0c01ca9d12ee	Spectrum
GC-MS	Heptanal, non-derivatized, GC-MS Spectrum	splash10-0006-9000000000-183283cb2427145b7678	Spectrum
GC-MS	Heptanal, non-derivatized, GC-MS Spectrum	splash10-0006-9000000000-aedf02ade0aa5bd82d71	Spectrum
GC-MS	Heptanal, non-derivatized, GC-MS Spectrum	splash10-0006-9000000000-a85809c1e2c6b7471781	Spectrum
GC-MS	Heptanal, non-derivatized, GC-MS Spectrum	splash10-006x-9000000000-d026c39b0c01ca9d12ee	Spectrum
Predicted GC-MS	Heptanal, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-056u-9000000000-721c1006ed41ad91802f	Spectrum
Predicted GC-MS	Heptanal, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-4900000000-66f451ed07dec07dc2bd	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-014j-9300000000-f683fbeaae9661c3375f	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-9000000000-62e7748838e417c074ba	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-1900000000-242e518285d8711c88d3	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-4900000000-2b9ed46fa89f52e6874e	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-614ce9045eac88449a8a	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4l-9000000000-e5c26cac568c7e70be7f	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-052f-9000000000-0497fb39284b3eae18e7	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-7f7db6b93b3268b34898	2021-09-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-03di-0900000000-87ba7764343ecec4c93f	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-03di-4900000000-baad9901fa250e031cb5	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052f-9000000000-8ffddb005d2cb639ad09	2021-09-23	View Spectrum

NMR

Type	Description	View
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	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

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
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

HMDB0031475

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Heptanal

METLIN ID

Not Available

PubChem Compound

8130

PDB ID

Not Available

ChEBI ID

34787

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 ]
Oenning AL, Mores L, Dias AN, Carasek E: A new configuration for bar adsorptive microextraction (BAmuE) for the quantification of biomarkers (hexanal and heptanal) in human urine by HPLC providing an alternative for early lung cancer diagnosis. Anal Chim Acta. 2017 May 1;965:54-62. doi: 10.1016/j.aca.2017.02.034. Epub 2017 Mar 6. [PubMed:28366212 ]

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 Heptanal (CDB000072)

Structure for CDB000072 (Heptanal)

Transporters