beta-Ionone (YMDB01643)

Identification

YMDB ID

YMDB01643

Name

beta-Ionone

Species

Saccharomyces cerevisiae

Strain

Brewer's yeast

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. Based on a literature review a significant number of articles have been published on beta-Ionone.

Structure

MOL SDF PDB SMILES InChI

Synonyms

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

CAS number

79-77-6

Weight

Average: 192.2973
Monoisotopic: 192.151415262

InChI Key

PSQYTAPXSHCGMF-BQYQJAHWSA-N

InChI

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+

IUPAC Name

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

Traditional IUPAC Name

β-ionone

Chemical Formula

C₁₃H₂₀O

SMILES

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

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 )

Physical Properties

State

Solid

Charge

Melting point

-49 °C

Experimental Properties

Property	Value	Reference
Water Solubility	Not Available	PhysProp
LogP	Not Available	PhysProp

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	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Biological Properties

Cellular Locations

Not Available

Organoleptic Properties

Flavour/Odour	Source
Dry	FDB015469
Floral	FDB015469
Flower	FDB015469
Jam	FDB015469
Orange	FDB015469
Orris	FDB015469
Powdery	FDB015469
Raspberry	FDB015469
Seaweed	FDB015469
Violet	FDB015469
Woody	FDB015469

SMPDB Pathways

Not Available

KEGG Pathways

Not Available

SMPDB Reactions

Not Available

KEGG Reactions

Not Available

Concentrations

Intracellular Concentrations

Not Available

Extracellular Concentrations

Not Available

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-002f-8900000000-c13b694647d1f5e201bf	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-004i-3900000000-b2fd6907056260485dd2	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-004l-9800000000-3e2f914b8442dedd62d9	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-004l-6900000000-a0ed0929b7cb7526955d	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-004l-4900000000-3169016f24891f9035d6	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-002f-8900000000-c13b694647d1f5e201bf	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-004i-3900000000-b2fd6907056260485dd2	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-004l-9800000000-3e2f914b8442dedd62d9	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-004l-6900000000-a0ed0929b7cb7526955d	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-004l-4900000000-3169016f24891f9035d6	JSpectraViewer \| MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-004j-2900000000-00c10c6b19261d08ffea	JSpectraViewer
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-002f-0900000000-0f7a122ff9743bcbf077	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-004u-4900000000-9dad39944d71a20a0f87	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0gbc-9400000000-77a4b4a15731ccc83316	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0900000000-b62117da7fb50997c027	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0006-0900000000-e7133a7253517651678a	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-05ed-3900000000-c1d86be9896bad6ad97e	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-1900000000-2dfc2141d793c1b81afc	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-05gl-7900000000-4e2d786c5425c33577a5	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-052f-9500000000-66ef449f7e5f91221704	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0006-0900000000-14436e4d9ff8d032db54	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0007-0900000000-85f77f47306d55836911	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0002-1900000000-5f53d8abc51bbf1e4e99	JSpectraViewer
MS	Mass Spectrum (Electron Ionization)	splash10-004l-6900000000-9288b23b92d86ede5336	JSpectraViewer \| MoNA
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer
1D NMR	13C NMR Spectrum	Not Available	JSpectraViewer
1D NMR	1H NMR Spectrum	Not Available	JSpectraViewer

References

References:

Loscos, N., Hernandez-Orte, P., Cacho, J., Ferreira, V. (2007). "Release and formation of varietal aroma compounds during alcoholic fermentation from nonfloral grape odorless flavor precursors fractions." J Agric Food Chem 55:6674-6684.17616208

Synthesis Reference:

Not Available

External Links:

Resource	Link
CHEBI ID	32325
HMDB ID	HMDB0036565
Pubchem Compound ID	26955
Kegg ID	C12287
ChemSpider ID	553581
FOODB ID	FDB015469
Wikipedia ID	Ionone
BioCyc ID	Not Available

Structure for #<Compound:0xb0875108>