Citral (YMDB01656)

Identification

YMDB ID

YMDB01656

Name

Citral

Species

Saccharomyces cerevisiae

Strain

Brewer's yeast

Description

Geranial, also known as (2E)-geranial or alpha-citral, belongs to the class of organic compounds known as acyclic monoterpenoids. These are monoterpenes that do not contain a cycle. Thus, geranial is considered to be an isoprenoid. Based on a literature review a significant number of articles have been published on Geranial.

Structure

MOL SDF PDB SMILES InChI

Synonyms

(2E)-3,7-Dimethyl-2,6-octadienal
2, 6-Octadienal, 3,7-dimethyl-
2,6-Octadienal, 3,7-dimethyl-
3,7-Dimethyl-1,2, 6-octadienal
3,7-Dimethyl-1,2,6-octadienal
3,7-Dimethyl-2,6-octadienal
cis-Citral
cis,trans-Citral
Citral (cis and trans)
Citral acis-3,7-dimethyl-2,6-octadienal
Geranial
Lemarome n
Neral
trans-Citral
Z-3,7-Dimethyl-2,6-octadiene-1-al
(2E)-Geranial
(e)-Citral
(e)-Geranial
alpha-Citral
Citral a
Lemonal
a-Citral
Α-citral
(e)-3,7-Dimethyl-2,6-octadienal
(e)-3,7-Dimethylocta-2,6-dienal
3,7-Dimethyl-(2E)-2,6-octadienal
3,7-Dimethyl-(e)-2,6-octadienal
3,7-Dimethyl-trans-2,6-octadienal
alpha -Citral
beta-Geranial
Citral-a
Genanial
Geranal
trans-3,7-Dimethyl-2,6-octadienal
(Z)-Citral
Citral
(2E)-3,7-Dimethyl-2,6-octadien-1-al
(E)-Neral
Geranaldehyde
beta-Neral
trans-3,7-Dimethyl-2,6-octadien-1-al
trans-Geranial
β-Geranial
β-Neral
3,7-Dimethyl-2,6-octadien-1-al

CAS number

5392-40-5

Weight

Average: 152.2334
Monoisotopic: 152.120115134

InChI Key

WTEVQBCEXWBHNA-JXMROGBWSA-N

InChI

InChI=1S/C10H16O/c1-9(2)5-4-6-10(3)7-8-11/h5,7-8H,4,6H2,1-3H3/b10-7+

IUPAC Name

(2E)-3,7-dimethylocta-2,6-dienal

Traditional IUPAC Name

α-citral

Chemical Formula

C₁₀H₁₆O

SMILES

CC(C)=CCC\C(C)=C\C=O

Chemical Taxonomy

Description

belongs to the class of organic compounds known as acyclic monoterpenoids. These are monoterpenes that do not contain a cycle.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Acyclic monoterpenoids

Alternative Parents

Substituents

Acyclic monoterpenoid
Medium-chain aldehyde
Enal
Alpha,beta-unsaturated aldehyde
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aldehyde
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

enal (CHEBI:16980 )
monoterpenoid (CHEBI:16980 )
Acyclic monoterpenoids (C01499 )
Linear monoterpenes (C01499 )
Acyclic monoterpenoids (LMPR0102010003 )

Physical Properties

State

Liquid

Charge

Melting point

<-10 °C

Experimental Properties

Property	Value	Reference
Water Solubility	1.34 mg/mL at 37 oC [YALKOWSKY,SH & HE,Y (2003)]	PhysProp
LogP	Not Available	PhysProp

Predicted Properties

Property	Value	Source
Water Solubility	0.4 g/L	ALOGPS
logP	3.37	ALOGPS
logP	2.66	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Basic)	-4.1	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	50.12 m³·mol⁻¹	ChemAxon
Polarizability	18.6 Å³	ChemAxon
Number of Rings	0	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
Bitter	FDB013702
Lemon	FDB013702
Sharp	FDB013702
Sweet	FDB013702

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)	splash10-014l-9000000000-ccb0a3f327b5d2362bb9	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-014i-9100000000-131249cb1d7fb343fe10	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-014i-9100000000-dcdfd8342f2d4ce5a439	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-014i-9100000000-3c1a8e898f563c833b2c	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-00kf-9000000000-90723459c49195367705	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-014l-9000000000-ccb0a3f327b5d2362bb9	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-014i-9100000000-131249cb1d7fb343fe10	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-014i-9100000000-dcdfd8342f2d4ce5a439	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-014i-9100000000-3c1a8e898f563c833b2c	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-00kf-9000000000-90723459c49195367705	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-014l-9000000000-ccb0a3f327b5d2362bb9	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-014i-9100000000-131249cb1d7fb343fe10	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-014i-9100000000-dcdfd8342f2d4ce5a439	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-014i-9100000000-3c1a8e898f563c833b2c	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-00kf-9000000000-90723459c49195367705	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-014l-9000000000-ccb0a3f327b5d2362bb9	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-014i-9100000000-131249cb1d7fb343fe10	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-014i-9100000000-dcdfd8342f2d4ce5a439	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-014i-9100000000-3c1a8e898f563c833b2c	JSpectraViewer \| MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-00kf-9000000000-90723459c49195367705	JSpectraViewer \| MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0159-9300000000-625c688e32f3edaf287c	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	splash10-0udi-1900000000-84bd30b4e03200f6db52	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-1010-8900000000-8aa62bcc7a1bcaa41a1e	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0gb9-9000000000-79a3e6745a117da8309b	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0900000000-21d238fd55ee29af690f	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-1900000000-b84583833bad67467cf0	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-052f-9700000000-a5e231c57e7f56a65d6d	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0pb9-0900000000-70e7a03f5a911f54f098	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-0900000000-3128155f72d867d46318	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-014i-9100000000-9b92fab117afca4b3a0a	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-05o0-9100000000-9c5fcd575fed478bccf6	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-05qc-9000000000-85ae79bf95f3094e7a85	JSpectraViewer
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00kf-9000000000-1a9a16cf8ea66689ce6a	JSpectraViewer
MS	Mass Spectrum (Electron Ionization)	splash10-014l-9100000000-92c761fd6ee64c67e40e	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:

Not Available

Synthesis Reference:

Not Available

External Links:

Resource	Link
CHEBI ID	16980
HMDB ID	HMDB0035078
Pubchem Compound ID	8843
Kegg ID	C01499
ChemSpider ID	553578
FOODB ID	FDB013702
Wikipedia ID	Citral
BioCyc ID	Not Available

Structure for #<Compound:0x8b95dc70>