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Tiglic acid (FDB000774)

Record Information
Version1.0
Creation date2010-04-08 22:04:42 UTC
Update date2019-11-26 02:55:23 UTC
Primary IDFDB000774
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameTiglic acid
DescriptionFlavouring ingredient A thick, syrupy poisonous liquid, C5H8O2, derived from croton oil, having a spicy odor and used in making perfumes and flavoring agents.; Tiglic acid has a double bond between the second and third carbons of the chain. Together with angelic acid form a pair of cis-trans isomers. Tiglic acid is a volatile and crystallizable substance with a sweet, warm spicy odour. It is used in making perfumes and flavoring agents.; Tiglic acid is a monocarboxylic unsaturated organic acid. It is found in croton oil and in several other natural products. It was also isolated from the defensive secretion of certain beetles.; Tiglic acid is a skin and eye irritant. The inhalation of the substance causes respiratory tract irritation. It is listed on the Toxic Substances Control Act (TSCA).
CAS Number80-59-1
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
SynonymSource
Not AvailableNot Available
Predicted Properties
PropertyValueSource
logP1.32ChemAxon
pKa (Strongest Acidic)4.97ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity27.32 m³·mol⁻¹ChemAxon
Polarizability10.35 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC5H8O2
IUPAC name(2Z)-2-methylbut-2-enoic acid
InChI IdentifierInChI=1S/C5H8O2/c1-3-4(2)5(6)7/h3H,1-2H3,(H,6,7)/b4-3-
InChI KeyUIERETOOQGIECD-ARJAWSKDSA-N
Isomeric SMILESC\C=C(\C)C(O)=O
Average Molecular Weight100.1158
Monoisotopic Molecular Weight100.0524295
Classification
Description Belongs to the class of organic compounds known as methyl-branched fatty acids. These are fatty acids with an acyl chain that has a methyl branch. Usually, they are saturated and contain only one or more methyl group. However, branches other than methyl may be present.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentMethyl-branched fatty acids
Alternative Parents
Substituents
  • Methyl-branched fatty acid
  • Unsaturated fatty acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physico-Chemical Properties
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateLiquid
Physical DescriptionNot Available
Mass CompositionC 59.98%; H 8.05%; O 31.96%DFC
Melting PointMp 63.5-64°DFC
Boiling PointBp11.5 95-96°DFC
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKapKa 4.96 (18°)DFC
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSTiglic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0zi0-9000000000-4314e75ba9656b7fb97fSpectrum
Predicted GC-MSTiglic acid, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0ab9-9200000000-1e8cf22de89b50fd327dSpectrum
Predicted GC-MSTiglic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSTiglic acid, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-8900000000-68b09835981f85d65f902016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9100000000-7999b5228e0df947f9492016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-179be6ce006eb4e9f0842016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-9000000000-357a7c774a32d7c0444f2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4j-9000000000-78eae8b34531c3c1bc272016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-9000000000-eb61c33f642ca5d4e6762016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-9000000000-0cc8aed45af20d83ec922021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9000000000-821598b1a2e8057a35672021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4r-9000000000-5e5e9fc82472025ff5032021-09-23View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-9000000000-5289cc75fe7aae11de792021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000t-9000000000-16cd54f70787a892bf2b2021-09-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9000000000-59b712b76240ebaa68882021-09-25View Spectrum
NMRNot Available
ChemSpider ID111629
ChEMBL IDCHEMBL52416
KEGG Compound IDC08279
Pubchem Compound ID125468
Pubchem Substance IDNot Available
ChEBI ID9592
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB01470
CRC / DFC (Dictionary of Food Compounds) IDBHB40-W:BHB42-Y
EAFUS ID2273
Dr. Duke IDTIGLIC-ACID
BIGG IDNot Available
KNApSAcK IDC00001207
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDrw1010371
SuperScent IDNot Available
Wikipedia IDTiglic acid
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
perfumery48318 A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
sweet
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
dry
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
spicy
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
woody
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
caramel
  1. The Good Scents Company (2009). Flavor and fragrance information catalog. <http://www.thegoodscentscompany.com/allprod.html> Accessed 15.10.23.
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.