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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 21:07:50 UTC
Update Date2022-03-07 02:54:45 UTC
HMDB IDHMDB0036061
Secondary Accession Numbers
  • HMDB36061
Metabolite Identification
Common NameSafranal
DescriptionSafranal is found in fig. Safranal is a constituent of saffron (Crocus sativa). Safranal is a flavouring ingredient It is believed that safranal is a degradation product of the carotenoid zeaxanthin via the intermediacy of picrocrocin. Safranal is an effective anticonvulsant shown to act as an agonist at GABAA receptors. Safranal also exhibits high antioxidant and free radical scavenging activity, along with cytotoxicity towards cancer cells in vitro. It has also been shown to have antidepressant properties. Safranal is an organic compound isolated from saffron, the spice consisting of the stigmas of crocus flowers (Crocus sativus). It is the constituent primarily responsible for the aroma of saffron
Structure
Data?1563862815
Synonyms
ValueSource
(2,6,6-Trimethylcyclohexa-1,3-dienyl)methanalChEBI
1,1,3-Trimethyl-2-formylcyclohexa-2,4-dieneChEBI
2,6,6-Trimethyl-1,3-cyclohexadiene-1-carboxaldehydeChEBI
2,6,6-Trimethylcyclohexa-1,3-dienyl methanalChEBI
Dehydro-beta-cyclocitralChEBI
Dehydro-b-cyclocitralGenerator
Dehydro-β-cyclocitralGenerator
1-Formyl-2,6,6-trimethyl-1,3-cyclohexadieneHMDB
2,3-dihydro-2,2,6-TrimethylbenzaldehydeHMDB
2,6,6-Trimethyl-1,3-cyclohexadienalHMDB
2,6,6-Trimethyl-1,3-cyclohexadiene-1-carbaldehydeHMDB
2,6,6-Trimethyl-1,3-cyclohexadienecarboxaldehyde, 9ciHMDB
FEMA 3389HMDB
Chemical FormulaC10H14O
Average Molecular Weight150.2176
Monoisotopic Molecular Weight150.10446507
IUPAC Name2,6,6-trimethylcyclohexa-1,3-diene-1-carbaldehyde
Traditional Namesafranal
CAS Registry Number116-26-7
SMILES
CC1=C(C=O)C(C)(C)CC=C1
InChI Identifier
InChI=1S/C10H14O/c1-8-5-4-6-10(2,3)9(8)7-11/h4-5,7H,6H2,1-3H3
InChI KeySGAWOGXMMPSZPB-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as organic oxides. These are organic compounds containing an oxide group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganic oxides
Sub ClassNot Available
Direct ParentOrganic oxides
Alternative Parents
Substituents
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aldehyde
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point< 25 °CNot Available
Boiling Point70.00 °C. @ 1.00 mm HgThe Good Scents Company Information System
Water Solubility134.2 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP2.825 (est)The Good Scents Company Information System
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.36 g/LALOGPS
logP2.93ALOGPS
logP2.05ChemAxon
logS-2ALOGPS
pKa (Strongest Basic)-4.3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area17.07 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity48.22 m³·mol⁻¹ChemAxon
Polarizability17.32 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+134.07431661259
DarkChem[M-H]-129.98831661259
DeepCCS[M+H]+138.33630932474
DeepCCS[M-H]-135.41430932474
DeepCCS[M-2H]-171.74430932474
DeepCCS[M+Na]+147.28130932474
AllCCS[M+H]+129.932859911
AllCCS[M+H-H2O]+125.432859911
AllCCS[M+NH4]+134.132859911
AllCCS[M+Na]+135.332859911
AllCCS[M-H]-132.732859911
AllCCS[M+Na-2H]-134.232859911
AllCCS[M+HCOO]-135.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
SafranalCC1=C(C=O)C(C)(C)CC=C11619.0Standard polar33892256
SafranalCC1=C(C=O)C(C)(C)CC=C11122.3Standard non polar33892256
SafranalCC1=C(C=O)C(C)(C)CC=C11162.3Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Safranal GC-MS (Non-derivatized) - 70eV, Positivesplash10-0kg9-2900000000-b082ebe4ee4447dc79802017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Safranal GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Safranal GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Safranal 10V, Positive-QTOFsplash10-0udi-0900000000-b34ca14deaad2e3be8c42016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Safranal 20V, Positive-QTOFsplash10-0uxr-9700000000-317a87cd8595a79b42d02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Safranal 40V, Positive-QTOFsplash10-0gb9-9100000000-2993b4b7b24364148faf2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Safranal 10V, Negative-QTOFsplash10-0002-0900000000-e83c23e4fe0dedd738e72016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Safranal 20V, Negative-QTOFsplash10-0002-0900000000-648f823a03c6712751e02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Safranal 40V, Negative-QTOFsplash10-05ng-8900000000-b0e87ace4983e8eca5152016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Safranal 10V, Negative-QTOFsplash10-00di-0900000000-b7cb4601ae2fb08997c12021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Safranal 20V, Negative-QTOFsplash10-00dj-0900000000-449dca9897e0f32093242021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Safranal 40V, Negative-QTOFsplash10-0a4i-0900000000-861947f0491f909a25882021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Safranal 10V, Positive-QTOFsplash10-0zfr-4900000000-f591f9acd9c148c93dd02021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Safranal 20V, Positive-QTOFsplash10-0a4i-9800000000-066e7f2d59fb906577f82021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Safranal 40V, Positive-QTOFsplash10-0ar0-9300000000-c8eb85059ddf025ee54a2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB014884
KNApSAcK IDC00035737
Chemspider ID55000
KEGG Compound IDC17062
BioCyc IDCPD-8669
BiGG IDNot Available
Wikipedia LinkSafranal
METLIN IDNot Available
PubChem Compound61041
PDB IDNot Available
ChEBI ID53169
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1016371
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Hosseinzadeh H, Sadeghnia HR: Protective effect of safranal on pentylenetetrazol-induced seizures in the rat: involvement of GABAergic and opioids systems. Phytomedicine. 2007 Apr;14(4):256-62. Epub 2006 May 16. [PubMed:16707256 ]
  2. Boskabady MH, Aslani MR: Relaxant effect of Crocus sativus (saffron) on guinea-pig tracheal chains and its possible mechanisms. J Pharm Pharmacol. 2006 Oct;58(10):1385-90. [PubMed:17034662 ]
  3. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .