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Showing NP-Card for Tiglic acid (NP0000703)

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Record Information
Version1.0
Created at2005-11-16 15:48:42 UTC
Updated at2021-08-19 23:58:21 UTC
NP-MRD IDNP0000703
Secondary Accession NumbersNone
Natural Product Identification
Common NameTiglic acid
DescriptionTiglic acid is a monocarboxylic unsaturated organic acid. It is found in croton oil and in several other natural products. It has also been isolated from the defensive secretion of certain beetles. Tiglic acid, also known as tiglate or tiglinsaeure, 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. Tiglic acid has a double bond between the second and third carbons of the chain. Tiglic acid and 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. The salts and esters of tiglic acid are called tiglates.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for NP0000703 (Tiglic acid)


  Mrv1652305271900302D          

  7  6  0  0  0  0            999 V2000
    0.1029   -0.1750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6140    0.2333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8160    0.2333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1029   -1.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3272   -0.1750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6140    1.0596    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5330   -0.1750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  2  0  0  0  0
  1  4  1  0  0  0  0
  2  5  1  0  0  0  0
  2  6  2  0  0  0  0
  3  7  1  0  0  0  0
M  END
Download

3D MOL for NP0000703 (Tiglic acid)

HMDB0001470
     RDKit          3D
Tiglic acid
 15 14  0  0  0  0  0  0  0  0999 V2000
   -1.9830   -0.5252   -0.2504 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5968   -1.0219   -0.0662 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3460   -0.1004    0.0964 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0064    1.3321    0.0882 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7220   -0.5405    0.2808 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0075   -1.7782    0.2852 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6934    0.4237    0.4488 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6180   -1.4254   -0.4930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0943    0.1618   -1.1000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4109   -0.1207    0.7011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3523   -2.0914   -0.0628 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9277    1.8996   -0.0997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4264    1.6808    1.0617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7033    1.6067   -0.7287 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4948    0.4991   -0.1615 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  3  5  1  0
  5  6  2  0
  5  7  1  0
  1  8  1  0
  1  9  1  0
  1 10  1  0
  2 11  1  0
  4 12  1  0
  4 13  1  0
  4 14  1  0
  7 15  1  0
M  END
Download

3D SDF for NP0000703 (Tiglic acid)


  Mrv1652305271900302D          

  7  6  0  0  0  0            999 V2000
    0.1029   -0.1750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6140    0.2333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8160    0.2333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1029   -1.0013    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3272   -0.1750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6140    1.0596    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5330   -0.1750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  2  0  0  0  0
  1  4  1  0  0  0  0
  2  5  1  0  0  0  0
  2  6  2  0  0  0  0
  3  7  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0000703

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C=C(/C)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C5H8O2/c1-3-4(2)5(6)7/h3H,1-2H3,(H,6,7)/b4-3+

> <INCHI_KEY>
UIERETOOQGIECD-ONEGZZNKSA-N

> <FORMULA>
C5H8O2

> <MOLECULAR_WEIGHT>
100.1158

> <EXACT_MASS>
100.0524295

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
15

> <JCHEM_AVERAGE_POLARIZABILITY>
10.386001376060808

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2E)-2-methylbut-2-enoic acid

> <ALOGPS_LOGP>
1.13

> <JCHEM_LOGP>
1.3151327766666667

> <ALOGPS_LOGS>
-0.08

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.971335232759619

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
27.322000000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.30e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
tiglic acid

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for NP0000703 (Tiglic acid)

HMDB0001470
     RDKit          3D
Tiglic acid
 15 14  0  0  0  0  0  0  0  0999 V2000
   -1.9830   -0.5252   -0.2504 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5968   -1.0219   -0.0662 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3460   -0.1004    0.0964 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0064    1.3321    0.0882 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7220   -0.5405    0.2808 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0075   -1.7782    0.2852 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6934    0.4237    0.4488 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6180   -1.4254   -0.4930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0943    0.1618   -1.1000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4109   -0.1207    0.7011 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3523   -2.0914   -0.0628 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9277    1.8996   -0.0997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4264    1.6808    1.0617 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7033    1.6067   -0.7287 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4948    0.4991   -0.1615 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  3  5  1  0
  5  6  2  0
  5  7  1  0
  1  8  1  0
  1  9  1  0
  1 10  1  0
  2 11  1  0
  4 12  1  0
  4 13  1  0
  4 14  1  0
  7 15  1  0
M  END
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PDB for NP0000703 (Tiglic acid)

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0       0.192  -0.327   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.146   0.435   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.523   0.435   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.192  -1.869   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -2.477  -0.327   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      -1.146   1.978   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       2.862  -0.327   0.000  0.00  0.00           C+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5    6                                                  
CONECT    3    1    7                                                       
CONECT    4    1                                                            
CONECT    5    2                                                            
CONECT    6    2                                                            
CONECT    7    3                                                            
MASTER        0    0    0    0    0    0    0    0    7    0   12    0
END
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3D PDB for NP0000703 (Tiglic acid)

COMPND    HMDB0001470
HETATM    1  C1  UNL     1      -1.983  -0.525  -0.250  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.597  -1.022  -0.066  1.00  0.00           C  
HETATM    3  C3  UNL     1       0.346  -0.100   0.096  1.00  0.00           C  
HETATM    4  C4  UNL     1      -0.006   1.332   0.088  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.722  -0.541   0.281  1.00  0.00           C  
HETATM    6  O1  UNL     1       2.007  -1.778   0.285  1.00  0.00           O  
HETATM    7  O2  UNL     1       2.693   0.424   0.449  1.00  0.00           O  
HETATM    8  H1  UNL     1      -2.618  -1.425  -0.493  1.00  0.00           H  
HETATM    9  H2  UNL     1      -2.094   0.162  -1.100  1.00  0.00           H  
HETATM   10  H3  UNL     1      -2.411  -0.121   0.701  1.00  0.00           H  
HETATM   11  H4  UNL     1      -0.352  -2.091  -0.063  1.00  0.00           H  
HETATM   12  H5  UNL     1       0.928   1.900  -0.100  1.00  0.00           H  
HETATM   13  H6  UNL     1      -0.426   1.681   1.062  1.00  0.00           H  
HETATM   14  H7  UNL     1      -0.703   1.607  -0.729  1.00  0.00           H  
HETATM   15  H8  UNL     1       3.495   0.499  -0.161  1.00  0.00           H  
CONECT    1    2    8    9   10
CONECT    2    3    3   11
CONECT    3    4    5
CONECT    4   12   13   14
CONECT    5    6    6    7
CONECT    7   15
END
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SMILES for NP0000703 (Tiglic acid)

C\C=C(/C)C(O)=O
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INCHI for NP0000703 (Tiglic acid)

InChI=1S/C5H8O2/c1-3-4(2)5(6)7/h3H,1-2H3,(H,6,7)/b4-3+
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View in JSmol
Synonyms
ValueSource
(e)-2,3-Dimethylacrylic acidChEBI
(e)-2-Methylbut-2-enoic acidChEBI
(e)-2-Methylcrotonic acidChEBI
Methyl methacrylic acidChEBI
TiglinsaeureChEBI
trans-2,3-Dimethylacrylic acidChEBI
trans-2-Methyl-2-butenoic acidChEBI
trans-2-Methylcrotonic acidChEBI
trans-alpha,beta-Dimethylacrylic acidChEBI
(e)-2,3-DimethylacrylateGenerator
(e)-2-Methylbut-2-enoateGenerator
(e)-2-MethylcrotonateGenerator
Methyl methacrylateGenerator
trans-2,3-DimethylacrylateGenerator
trans-2-Methyl-2-butenoateGenerator
trans-2-MethylcrotonateGenerator
trans-a,b-DimethylacrylateGenerator
trans-a,b-Dimethylacrylic acidGenerator
trans-alpha,beta-DimethylacrylateGenerator
trans-Α,β-dimethylacrylateGenerator
trans-Α,β-dimethylacrylic acidGenerator
TiglateGenerator
(2E)-2-Methyl-2-butenoateHMDB
(2E)-2-Methyl-2-butenoic acidHMDB
(e)-2-Methyl-2-butenoateHMDB
(e)-2-Methyl-2-butenoic acidHMDB
(e)-2-Methyl-crotonateHMDB
(e)-2-Methyl-crotonic acidHMDB
2,3-DimethylacrylateHMDB
2,3-Dimethylacrylic acidHMDB
2-Methyl-(e)-2-butenoateHMDB
2-Methyl-(e)-2-butenoic acidHMDB
2-Methyl-2-butenoateHMDB
2-Methyl-2-butenoic acidHMDB
2-Methyl-crotonateHMDB
2-Methyl-crotonic acidHMDB
2-Methylbut-2-enoateHMDB
2-Methylbut-2-enoic acidHMDB
CevadateHMDB
Cevadic acidHMDB
e-TiglateHMDB
e-Tiglic acidHMDB
epsilon-TiglateHMDB
epsilon-Tiglic acidHMDB
MethylbutenoicacidHMDB
TiglinateHMDB
Tiglinic acidHMDB
trans-2-Methylcrotonic acid = trans-2-methyl-2-butenoateHMDB
trans-2-Methylcrotonic acid = trans-2-methyl-2-butenoic acidHMDB
trans-2-Methylcrotonic acid = trans-2-methyl-2-butenoic acid = tiglinateHMDB
trans-2-Methylcrotonic acid = trans-2-methyl-2-butenoic acid = tiglinic acidHMDB
Tiglic acid, (Z)-isomerHMDB
Tiglic acid, (e)-isomerHMDB
Chemical FormulaC5H8O2
Average Mass100.1158 Da
Monoisotopic Mass100.05243 Da
IUPAC Name(2E)-2-methylbut-2-enoic acid
Traditional Nametiglic acid
CAS Registry Number80-59-1
SMILES
C\C=C(/C)C(O)=O
InChI Identifier
InChI=1S/C5H8O2/c1-3-4(2)5(6)7/h3H,1-2H3,(H,6,7)/b4-3+
InChI KeyUIERETOOQGIECD-ONEGZZNKSA-N
Experimental Spectra
Spectrum TypeDescriptionDepositor EmailDepositor OrganizationDepositorDeposition DateView
1D NMR1H NMR Spectrum (1D, 500 MHz, 5%_DMSO, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Wishart LabWishart LabDavid Wishart2021-06-20View Spectrum
Predicted Spectra
Not Available
Chemical Shift Submissions
Not Available
Species
Species of Origin
Species NameSourceReference
Aloe africanaLOTUS Database
Anas platyrhynchosFooDB
AnatidaeFooDB
Angelica archangelicaKNApSAcK Database
Angelica pubescens f.biserrataKNApSAcK Database
Anser anserFooDB
Anthemis nobilisKNApSAcK Database
Apis ceranaLOTUS Database
Apium graveolensFooDB
Apium graveolens var. dulceFooDB
    • C. W. Wilson Relative Recovery and Identification of Carbonyl Compounds from Celery Essential Oil...
Arctium lappaFooDB
Arnebia hispidissimaPlant
Azadirachta indicaLOTUS Database
Bison bisonFooDB
Bos taurusFooDB
Bos taurus X Bison bisonFooDB
Bubalus bubalisFooDB
Capra aegagrus hircusFooDB
CervidaeFooDB
Cervus canadensisFooDB
Chamaemelum nobileFooDB
ColumbaFooDB
ColumbidaeFooDB
Croton tigliumKNApSAcK Database
Cuscuta chinensisKNApSAcK Database
Daucus carotaKNApSAcK Database
Daucus carota ssp. sativusFooDB
Dromaius novaehollandiaeFooDB
Equus caballusFooDB
Flavouring ingredient-
Gallus gallusFooDB
Lagopus mutaFooDB
LeporidaeFooDB
Lepus timidusFooDB
Ligularia pleurocaulisLOTUS Database
Lithospermum erythrorhizonLOTUS Database
Melanitta fuscaFooDB
Meleagris gallopavoFooDB
Numida meleagrisFooDB
OdocoileusFooDB
OryctolagusFooDB
Ovis ariesFooDB
Pelargonium graveolensLOTUS Database
Petasites albusPlant
PhasianidaeFooDB
Phasianus colchicusFooDB
Struthio camelusFooDB
Sus scrofaFooDB
Sus scrofa domesticaFooDB
Chemical Taxonomy
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
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point61 - 65 °CNot Available
Boiling Point95.00 to 96.00 °C. @ 12.00 mm HgThe Good Scents Company Information System
Water Solubility1 mg/mLNot Available
LogP1.076 (est)The Good Scents Company Information System
Predicted Properties
PropertyValueSource
Water Solubility83 g/LALOGPS
logP1.13ALOGPS
logP1.32ChemAxon
logS-0.08ALOGPS
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
Polarizability10.39 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
HMDB IDHMDB0001470
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB000774
KNApSAcK IDC00001207
Chemspider ID111629
KEGG Compound IDC08279
BioCyc IDCPD-7077
BiGG IDNot Available
Wikipedia LinkTiglic_acid
METLIN ID6261
PubChem Compound125468
PDB IDNot Available
ChEBI ID9592
Good Scents IDrw1010371
References
General References
  1. Leete E, Murrill JB: Biosynthesis of the tiglic acid moiety of meteloidine in Datura meteloides. Tetrahedron Lett. 1967 May;18:1727-30. [PubMed:6045963 ]
  2. Noda N, Kogetsu H, Kawasaki T, Miyahara K: Scammonins VII and VIII, two resin glycosides from Convolvulus scammonia. Phytochemistry. 1992 Aug;31(8):2761-6. doi: 10.1016/0031-9422(92)83626-a. [PubMed:1368419 ]
  3. Attygalle AB, Wu X, Will KW: Biosynthesis of tiglic, ethacrylic, and 2-methylbutyric acids in a carabid beetle, Pterostichus (Hypherpes) californicus. J Chem Ecol. 2007 May;33(5):963-70. doi: 10.1007/s10886-007-9276-3. Epub 2007 Apr 3. [PubMed:17404818 ]
  4. Du XM, Kohinata K, Kawasaki T, Guo YT, Miyahara K: Components of the ether-insoluble resin glycoside-like fraction from Cuscuta chinensis. Phytochemistry. 1998 Jul;48(5):843-50. doi: 10.1016/s0031-9422(97)00990-4. [PubMed:9664709 ]
  5. Swiatkowski M, Lanka S, Czylkowska A, Gas K, Sawicki M: Structural, Spectroscopic, Thermal, and Magnetic Properties of a New Dinuclear Copper Coordination Compound with Tiglic Acid. Materials (Basel). 2021 Apr 23;14(9). pii: ma14092148. doi: 10.3390/ma14092148. [PubMed:33922582 ]
  6. Delgado-Altamirano R, Garcia-Aguilera ME, Delgado-Dominguez J, Becker I, Rodriguez de San Miguel E, Rojas-Molina A, Esturau-Escofet N: (1)H NMR profiling and chemometric analysis as an approach to predict the leishmanicidal activity of dichloromethane extracts from Lantana camara (L.). J Pharm Biomed Anal. 2021 May 30;199:114060. doi: 10.1016/j.jpba.2021.114060. Epub 2021 Apr 3. [PubMed:33848915 ]
  7. Wang HQ, Ma SG, Lin MB, Hou Q, Ma M, Yu SS: Hydroxylated Ethacrylic and Tiglic Acid Derivatives from the Stems and Branches of Enkianthus chinensis and Their Potential Anti-inflammatory Activities. J Nat Prod. 2020 Oct 23;83(10):2867-2876. doi: 10.1021/acs.jnatprod.0c00286. Epub 2020 Oct 14. [PubMed:33052045 ]