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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-11 20:01:20 UTC

Update Date

2023-02-21 17:24:35 UTC

HMDB ID

HMDB0035078

Secondary Accession Numbers

HMDB35078

Metabolite Identification

Common Name

Geranial

Description

Geranial, also known as 3,7-dimethyl-2,6-octadienal, citral or lemonal, belongs to the class of organic compounds known as acyclic monoterpenoids. These are monoterpenes that do not contain a cycle. Thus, citral is considered to be an isoprenoid lipid. Two different isomers of 3,7-dimethyl-2,6-octadienal exist. The E-isomer or trans-isomer is known as geranial or citral A. The Z-isomer or cis-isomer is known as neral or citral B. 3,7-dimethyl-2,6-octadienal is a very hydrophobic molecule, practically insoluble in water, and relatively neutral. Citral is present in the oils of several plants, including lemon myrtle (90-98%), Litsea citrata (90%), Litsea cubeba, lemongrass (65-80%), lemon tea-tree (70-80%), Ocimum gratissimum, Lindera citriodora, Calypranthes parriculata, petitgrain, lemon verbena, lemon ironbark, lemon balm, lime, lemon and orange. Citral has also been reported to be found in Cannabis sativa (PMID:6991645 , 26657499 ). Citral has a strong lemon (citrus) odor. Neral's lemon odor is less intense, but sweeter. Citral is therefore an aroma compound used in perfumery for its citrus effect. Citral is also used as a flavor and for fortifying lemon oil. It has strong antimicrobial qualities (PMID:28974979 ) and pheromonal effects in nematodes and insects (PMID:26973536 ). Citral is used in the synthesis of vitamin A, lycopene, ionone, and methylionone (a compound used to mask the smell of smoke).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

COMPND    HMDB0035078
HETATM    1  C1  UNL     1      -2.434   1.355   0.221  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.595  -0.016  -0.306  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.852  -0.435  -0.955  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.609  -0.883  -0.200  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.346  -0.446   0.457  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.750  -0.611  -0.596  1.00  0.00           C  
HETATM    7  C7  UNL     1       2.056  -0.195  -0.019  1.00  0.00           C  
HETATM    8  C8  UNL     1       2.551  -0.912   1.161  1.00  0.00           C  
HETATM    9  C9  UNL     1       2.751   0.779  -0.538  1.00  0.00           C  
HETATM   10  C10 UNL     1       4.041   1.217   0.004  1.00  0.00           C  
HETATM   11  O1  UNL     1       4.686   2.159  -0.519  1.00  0.00           O  
HETATM   12  H1  UNL     1      -3.348   1.972   0.082  1.00  0.00           H  
HETATM   13  H2  UNL     1      -1.556   1.821  -0.303  1.00  0.00           H  
HETATM   14  H3  UNL     1      -2.208   1.405   1.298  1.00  0.00           H  
HETATM   15  H4  UNL     1      -3.686  -1.174  -1.784  1.00  0.00           H  
HETATM   16  H5  UNL     1      -4.538  -0.954  -0.241  1.00  0.00           H  
HETATM   17  H6  UNL     1      -4.418   0.401  -1.388  1.00  0.00           H  
HETATM   18  H7  UNL     1      -1.722  -1.899  -0.588  1.00  0.00           H  
HETATM   19  H8  UNL     1      -0.410   0.589   0.831  1.00  0.00           H  
HETATM   20  H9  UNL     1      -0.151  -1.172   1.287  1.00  0.00           H  
HETATM   21  H10 UNL     1       0.471  -0.034  -1.481  1.00  0.00           H  
HETATM   22  H11 UNL     1       0.736  -1.690  -0.868  1.00  0.00           H  
HETATM   23  H12 UNL     1       2.078  -1.909   1.239  1.00  0.00           H  
HETATM   24  H13 UNL     1       2.237  -0.329   2.068  1.00  0.00           H  
HETATM   25  H14 UNL     1       3.650  -1.081   1.154  1.00  0.00           H  
HETATM   26  H15 UNL     1       2.371   1.286  -1.395  1.00  0.00           H  
HETATM   27  H16 UNL     1       4.497   0.754   0.874  1.00  0.00           H  
CONECT    1    2   12   13   14
CONECT    2    3    4    4
CONECT    3   15   16   17
CONECT    4    5   18
CONECT    5    6   19   20
CONECT    6    7   21   22
CONECT    7    8    9    9
CONECT    8   23   24   25
CONECT    9   10   26
CONECT   10   11   11   27
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(2E)-Geranial	ChEBI
(e)-Citral	ChEBI
(e)-Geranial	ChEBI
alpha-Citral	ChEBI
Citral a	ChEBI
Lemonal	ChEBI
trans-Citral	ChEBI
a-Citral	Generator
Α-citral	Generator
(2E)-3,7-Dimethyl-2,6-octadienal	HMDB
(e)-3,7-Dimethyl-2,6-octadienal	HMDB
(e)-3,7-Dimethylocta-2,6-dienal	HMDB
3,7-Dimethyl-(2E)-2,6-octadienal	HMDB
3,7-Dimethyl-(e)-2,6-octadienal	HMDB
3,7-Dimethyl-trans-2,6-octadienal	HMDB
alpha -Citral	HMDB
beta-Geranial	HMDB
Citral-a	HMDB
Genanial	HMDB
Geranal	HMDB
trans-3,7-Dimethyl-2,6-octadienal	HMDB
(Z)-Citral	MeSH, HMDB
Citral	MeSH, HMDB
(2E)-3,7-Dimethyl-2,6-octadien-1-al	HMDB
(E)-3,7-Dimethyl-2,6-octadienal	HMDB
(E)-Neral	HMDB
Geranaldehyde	HMDB
Geranial	HMDB
beta-Neral	HMDB
trans-3,7-Dimethyl-2,6-octadien-1-al	HMDB
trans-Geranial	HMDB
β-Geranial	HMDB
β-Neral	HMDB
3,7-Dimethyl-2,6-octadien-1-al	HMDB
3,7-Dimethyl-2,6-octadienal	HMDB

Chemical Formula

C₁₀H₁₆O

Average Molecular Weight

152.237

Monoisotopic Molecular Weight

152.120115135

IUPAC Name

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

Traditional Name

α-citral

CAS Registry Number

141-27-5

SMILES

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

InChI Identifier

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

InChI Key

WTEVQBCEXWBHNA-JXMROGBWSA-N

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 )

Ontology

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	228.00 to 229.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	1340 mg/L @ 25 °C (exp)	The Good Scents Company Information System
LogP	3.450	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular 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	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	136.817	31661259
DarkChem	[M-H]-	132.849	31661259
DeepCCS	[M+H]+	139.83	30932474
DeepCCS	[M-H]-	136.945	30932474
DeepCCS	[M-2H]-	173.724	30932474
DeepCCS	[M+Na]+	149.009	30932474
AllCCS	[M+H]+	135.8	32859911
AllCCS	[M+H-H2O]+	131.7	32859911
AllCCS	[M+NH4]+	139.6	32859911
AllCCS	[M+Na]+	140.7	32859911
AllCCS	[M-H]-	135.7	32859911
AllCCS	[M+Na-2H]-	137.6	32859911
AllCCS	[M+HCOO]-	139.8	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	7.03 minutes	32390414
Predicted by Siyang on May 30, 2022	14.3576 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.55 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2181.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	444.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	184.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	282.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	71.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	490.9 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	626.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	78.9 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1198.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	455.4 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	998.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	408.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	333.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	388.9 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	508.1 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	11.6 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Geranial	CC(C)=CCC\C(C)=C\C=O	1681.3	Standard polar	33892256
Geranial	CC(C)=CCC\C(C)=C\C=O	1212.4	Standard non polar	33892256
Geranial	CC(C)=CCC\C(C)=C\C=O	1257.4	Semi standard non polar	33892256

Spectra

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Saliva

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	20809147	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Not Specified	Normal	24421258	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Citral

METLIN ID

Not Available

PubChem Compound

638011

PDB ID

Not Available

ChEBI ID

16980

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1003432

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Duarte MC, Figueira GM, Sartoratto A, Rehder VL, Delarmelina C: Anti-Candida activity of Brazilian medicinal plants. J Ethnopharmacol. 2005 Feb 28;97(2):305-11. Epub 2005 Jan 5. [PubMed:15707770 ]
Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
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 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for Geranial (HMDB0035078)

MOL for HMDB0035078 (Geranial)

3D MOL for HMDB0035078 (Geranial)

3D SDF for HMDB0035078 (Geranial)

3D-SDF for HMDB0035078 (Geranial)

PDB for HMDB0035078 (Geranial)

3D PDB for HMDB0035078 (Geranial)

SMILES for HMDB0035078 (Geranial)

INCHI for HMDB0035078 (Geranial)

Structure for HMDB0035078 (Geranial)

3D Structure for HMDB0035078 (Geranial)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized