Showing Compound beta-Ionone (FDB015469)

Record Information

Version

1.0

Creation date

2010-04-08 22:11:51 UTC

Update date

2020-09-17 15:30:10 UTC

Primary ID

FDB015469

Secondary Accession Numbers

Not Available

Chemical Information

FooDB 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. 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 ( https://doi.org/10.1533/9780857095725.1.231).

CAS Number

79-77-6

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Synonym	Source
(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
(3E)-4-(2,6,6-trimethylcyclohex-1-en-1-yl)but-3-en-2-one	biospider
(e)-b-Ionone	Generator
(e)-beta -Ionone	HMDB
(e)-beta-Ionone	ChEBI
(E)-beta-ionone	biospider
(e)-Β-ionone	Generator
(E)-β-ionone	biospider
(e)-β-ionone	Generator

Showing 1 to 10 of 40 entries

Predicted Properties

Property	Value	Source
Water Solubility	0.1 g/L	ALOGPS
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

Chemical Formula

C13H20O

IUPAC name

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

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

Isomeric SMILES

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

Average Molecular Weight

192.2973

Monoisotopic Molecular Weight

192.151415262

Classification

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

Process

Naturally occurring process:

Biological process:

Biochemical process:

Chemical reaction:

Lipid peroxidation

Biochemical pathway:

Lipid metabolism pathway

Cellular process:

Cell signaling

Role

Industrial application:

Food and nutrition:

Flavoring agent

Biological role:

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Bp24 150-151°	DFC
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	C 81.20%; H 10.48%; O 8.32%	DFC
Melting Point	Not Available
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

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

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

32325

Phenol-Explorer ID

Not Available

DrugBank ID

Not Available

HMDB ID

HMDB36565

CRC / DFC (Dictionary of Food Compounds) ID

KCN48-Y:KCN48-Y

EAFUS ID

1806

Dr. Duke ID

BETA-IONONE

BIGG ID

Not Available

KNApSAcK ID

C00029816

HET ID

ID3

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

GoodScent ID

SuperScent ID

Wikipedia ID

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

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Food	Content Range	Average	Reference

Processing...

Biological Effects and Interactions

Health Effects / Bioactivities

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Descriptor	ID	Definition	Reference
allergenic	50904	A chemical compound which causes the onset of an allergic reaction by interacting with any of the molecular pathways involved in an allergy.	DUKE
anti bacterial	33282	A substance that kills or slows the growth of bacteria.	DUKE
anti cariogenic	52217	Any substance introduced into a living organism with therapeutic or diagnostic purpose.	DUKE
anti melanomic	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
antioxidant	22586	A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides. In European countries, E-numbers for permitted antioxidant food additives are from E 300 to E 324.	CHEBI
antitumor	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
cancer preventive	35610	A substance that inhibits or prevents the proliferation of neoplasms.	DUKE
cytochrome-p450 inducer			DUKE
fungicide	24127	A substance used to destroy fungal pests.	DUKE
hypocholesterolemic			DUKE

Showing 1 to 10 of 13 entries

Enzymes

Not Available

Pathways

Not Available

Metabolism

Not Available

Biosynthesis

Not Available

Organoleptic Properties

Flavours

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Flavor	Citations
dry	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
floral	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
flower	Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
jam	Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
orange	Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
orris	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
powdery	The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
raspberry	Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0 Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695
seaweed	Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0
violet	Arn, H, Acree TE. “Flavornet: A database of aroma compounds based on odor potency in natural products”. Developments in Food Science 40 (1998): 27. doi:10.1016/S0167-4501(98)80029-0 Dunkel, M. et al. SuperScent – a database of flavors and scents. Nucleic Acids Research 2008, doi:10.1093/nar/gkn695