Cannabis Compound Database: Showing Compound Card for Beta-Ionone (CDB000068)

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Identification Taxonomy Ontology Physical properties Spectra Protein target Pathways Concentrations Links References enzymes (1) Show 2 proteins XML

Record Information

Version

1.0

Created at

2020-03-18 23:23:35 UTC

Updated at

2020-12-07 19:07:02 UTC

CannabisDB ID

CDB000068

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

Beta-Ionone

Description

Beta-ionone, also known as (e)-b-ionone or trans-beta-ionone, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Beta-ionone is a neutral compound. Beta-ionone has a dry, floral, and flower taste with a cedar wood-like scent. It is a naturally occurring organic compound found in a variety of essential oils, including rose oil, flowers from Boronia megastigma (brown boronia; doi: 10.21273/hortsci.30.4.876d) and coml oil and found in cannabis plants (PMID:6991645 ). Beta-ionone is found in highest concentrations in corns, tea, and carrots and in lower concentrations in hyssops, peppermints, and safflowers. Beta-ionone has also been detected in common grapes, sour cherries, common wheats, garden tomato, and wakames making beta-ionone a potential biomarker for the consumption of these foods. Beta-ionone is used as to make Vitamins A, E and K1. It is used as a fragrance in perfumes, cosmetics and personal care products, and household cleaners and detergents. Beta-ionone is used as a food flavoring in beverages,¬†ice¬†cream, baked goods and candies ( Ref:DOI ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(e)-beta-Ionone	ChEBI
beta-e-Ionone	ChEBI
beta-Ionon	ChEBI
trans-beta-Ionone	ChEBI
(e)-b-Ionone	Generator
(e)-Β-ionone	Generator
b-e-Ionone	Generator
Β-e-ionone	Generator
b-Ionon	Generator
Β-ionon	Generator
trans-b-Ionone	Generator
trans-Β-ionone	Generator
b-Ionone	Generator
Β-ionone	Generator
(3E)-4-(2,6,6-Trimethyl-1-cyclohexen-1-yl)-3-buten-2-one	HMDB
(3E)-4-(2,6,6-Trimethylcyclohex-1-en-1-yl)but-3-en-2-one	HMDB
(e)-beta -Ionone	HMDB
4-(2,6,6-Trimethyl-1-cyclohexen-1-yl)-(e)-3-buten-2-one	HMDB
beta -e-Ionone	HMDB
FEMA 2595	HMDB
Ionone, beta	HMDB
trans-beta -Ionone	HMDB
[e]-4-[2,6,6-Trimethyl-1-cyclohexen-1-yl]-3-buten-2-one	HMDB
4-(2,6,6-Trimethyl-1-cyclohexen-1-yl)-3-buten-2-one	MeSH, HMDB
beta-Ionone, (trans)-isomer	MeSH, HMDB

Chemical Formula

C₁₃H₂₀O

Average Molecular Weight

192.3

Monoisotopic Molecular Weight

192.1514

IUPAC Name

(3E)-4-(2,6,6-trimethylcyclohex-1-en-1-yl)but-3-en-2-one

Traditional Name

β-ionone

CAS Registry Number

79-77-6

SMILES

CC(=O)\C=C\C1=C(C)CCCC1(C)C

InChI Identifier

InChI=1S/C13H20O/c1-10-6-5-9-13(3,4)12(10)8-7-11(2)14/h7-8H,5-6,9H2,1-4H3/b8-7+

InChI Key

PSQYTAPXSHCGMF-BQYQJAHWSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Cyclofarsesane sesquiterpenoid
Megastigmane sesquiterpenoid
Sesquiterpenoid
Ionone derivative
Alpha,beta-unsaturated ketone
Enone
Acryloyl-group
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

ionone (CHEBI:32325 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Animal

Plant:

Biological location:

Cell and elements:

Extracellular

Subcellular:

Biofluid and excreta:

Saliva

Role

Industrial application:

Personal care products:

Perfuming agent

Food and nutrition:

Flavoring agent

Biological role:

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
logP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	4.11	ALOGPS
logP	3.28	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	19.71	ChemAxon
pKa (Strongest Basic)	-4.7	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	2	ChemAxon
Refractivity	61.82 m³·mol⁻¹	ChemAxon
Polarizability	23.36 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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)	splash10-004l-6900000000-9288b23b92d86ede5336	2014-10-20	View Spectrum
GC-MS	Beta-Ionone, non-derivatized, GC-MS Spectrum	splash10-002f-8900000000-c13b694647d1f5e201bf	Spectrum
GC-MS	Beta-Ionone, non-derivatized, GC-MS Spectrum	splash10-004i-3900000000-b2fd6907056260485dd2	Spectrum
GC-MS	Beta-Ionone, non-derivatized, GC-MS Spectrum	splash10-004l-9800000000-3e2f914b8442dedd62d9	Spectrum
GC-MS	Beta-Ionone, non-derivatized, GC-MS Spectrum	splash10-004l-6900000000-a0ed0929b7cb7526955d	Spectrum
GC-MS	Beta-Ionone, non-derivatized, GC-MS Spectrum	splash10-004l-4900000000-3169016f24891f9035d6	Spectrum
GC-MS	Beta-Ionone, non-derivatized, GC-MS Spectrum	splash10-002f-8900000000-c13b694647d1f5e201bf	Spectrum
GC-MS	Beta-Ionone, non-derivatized, GC-MS Spectrum	splash10-004i-3900000000-b2fd6907056260485dd2	Spectrum
GC-MS	Beta-Ionone, non-derivatized, GC-MS Spectrum	splash10-004l-9800000000-3e2f914b8442dedd62d9	Spectrum
GC-MS	Beta-Ionone, non-derivatized, GC-MS Spectrum	splash10-004l-6900000000-a0ed0929b7cb7526955d	Spectrum
GC-MS	Beta-Ionone, non-derivatized, GC-MS Spectrum	splash10-004l-4900000000-3169016f24891f9035d6	Spectrum
Predicted GC-MS	Beta-Ionone, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-004j-2900000000-00c10c6b19261d08ffea	Spectrum
Predicted GC-MS	Beta-Ionone, 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	splash10-002f-0900000000-0f7a122ff9743bcbf077	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004u-4900000000-9dad39944d71a20a0f87	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0gbc-9400000000-77a4b4a15731ccc83316	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0900000000-b62117da7fb50997c027	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-0900000000-e7133a7253517651678a	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-05ed-3900000000-c1d86be9896bad6ad97e	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-1900000000-2dfc2141d793c1b81afc	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-05gl-7900000000-4e2d786c5425c33577a5	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-9500000000-66ef449f7e5f91221704	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0900000000-14436e4d9ff8d032db54	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0007-0900000000-85f77f47306d55836911	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0002-1900000000-5f53d8abc51bbf1e4e99	2021-09-24	View Spectrum

NMR

Type	Description	View
1D NMR	¹³C NMR Spectrum (1D, 15.09 MHz, CDCl₃, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Spectrum

Pathways

Not Available

Protein Targets

Enzymes

Protein Name	Gene Name	Locus	Uniprot ID	Details
Beta,beta-carotene 9',10'-oxygenase	BCO2	11q23.1	Q9BYV7	details

Transporters

Not Available

Metal Bindings

Protein Name	Gene Name	Locus	Uniprot ID	Details
Beta,beta-carotene 9',10'-oxygenase	BCO2	11q23.1	Q9BYV7	details

Receptors

Not Available

Transcriptional Factors

Not Available

Concentrations Data

Not Available

External Links

HMDB ID

HMDB0036565

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

Ionone

METLIN ID

Not Available

PubChem Compound

638014

PDB ID

ID3

ChEBI ID

32325

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. Beta,beta-carotene 9',10'-oxygenase

General function:: Secondary metabolites biosynthesis, transport and catabolism
Specific function:: Asymmetrically cleaves beta-carotene at the 9',10' double bond resulting in the formation of beta-apo-10'-carotenal and beta-ionone. Besides beta-carotene, lycopene is also oxidatively cleaved. The apocarotenals formed by this enzyme may be the precursors for the biosynthesis of retinoic acid or exert unknown physiological effects.
Gene Name:: BCO2
Uniprot ID:: Q9BYV7
Molecular weight:: 61509.65

Showing Compound Card for Beta-Ionone (CDB000068)

Structure for CDB000068 (Beta-Ionone)

Enzymes