NP-MRD: Showing NP-Card for (9z,11z)-octadeca-9,11-dienoic acid (NP0244931)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-09-07 05:49:58 UTC

Updated at

2022-09-07 05:49:59 UTC

NP-MRD ID

NP0244931

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(9z,11z)-octadeca-9,11-dienoic acid

Description

Ricinenic acid, also known as ricinenate or rumenic acid, belongs to the class of organic compounds known as lineolic acids and derivatives. These are derivatives of lineolic acid. Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions. (9z,11z)-octadeca-9,11-dienoic acid is found in Carthamus oxyacanthus. Ricinenic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 52 51  0  0  0  0  0  0  0  0999 V2000
   -7.2874   -0.7422    1.5422 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7595   -1.1736    0.1906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1593    0.0425   -0.4766 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0373    0.5766    0.3862 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4200    1.7964   -0.2624 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2859    2.3499    0.5933 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2216    1.3777    0.7909 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9666    1.4958    0.4379 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4839    2.6678   -0.2204 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7569    2.7971   -0.5729 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9037    1.9712   -0.4589 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9854    0.6603    0.1414 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4455    0.1116    0.0947 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9693   -0.0435   -1.2849 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3340   -0.5390   -1.4913 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8122   -1.8434   -1.0668 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8652   -2.2563    0.3410 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4621   -3.6546    0.3622 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8075   -4.2485   -0.6745 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6183   -4.2702    1.5828 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2452   -1.2898    1.7162 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4638    0.3470    1.5887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5861   -1.1105    2.3132 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5789   -1.5952   -0.4198 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9536   -1.9376    0.2781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9499    0.8198   -0.6469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7468   -0.2444   -1.4665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3036   -0.2475    0.4955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4316    0.7852    1.3929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2031    2.5651   -0.3925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0358    1.4865   -1.2519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9391    3.2868    0.1564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7548    2.6666    1.5838 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5063    0.4339    1.2958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3424    0.6651    0.6725 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1969    3.5137   -0.4472 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9597    3.8086   -1.0887 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3995    1.9670   -1.5243 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7114    2.6152    0.0690 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4358   -0.1738   -0.3753 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8030    0.7121    1.2357 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3734   -0.9327    0.5281 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1149    0.7596    0.6906 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9884    1.0203   -1.7198 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2113   -0.5342   -1.9607 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0349    0.3000   -1.1646 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5006   -0.4947   -2.6322 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3122   -2.6899   -1.6631 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8881   -1.9380   -1.4608 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9560   -2.3674    0.9129 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6458   -1.6404    0.8551 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5641   -3.7897    2.4752 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 20  1  0
 18 19  2  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  2 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  0
  6 33  1  0
  7 34  1  0
  8 35  1  0
  9 36  1  0
 10 37  1  0
 11 38  1  0
 11 39  1  0
 12 40  1  0
 12 41  1  0
 13 42  1  0
 13 43  1  0
 14 44  1  0
 14 45  1  0
 15 46  1  0
 15 47  1  0
 16 48  1  0
 16 49  1  0
 17 50  1  0
 17 51  1  0
 20 52  1  0
M  END


  Mrv1572011241503062D          

 20 19  0  0  0  0            999 V2000
   -3.4322    3.7934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7177    3.3809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0033    3.7934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2888    3.3809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5743    3.7934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1401    3.3809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8546    3.7934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5691    3.3809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5691    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2836    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9980    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4270    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1414    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8559    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5704    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2849    2.5559    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9993    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7138    2.5559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9993    1.3184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 18 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0244931

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C18H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h7-10H,2-6,11-17H2,1H3,(H,19,20)/b8-7-,10-9-

> <INCHI_KEY>
JBYXPOFIGCOSSB-QRLRYFCNSA-N

> <FORMULA>
C18H32O2

> <MOLECULAR_WEIGHT>
280.452

> <EXACT_MASS>
280.24023027

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
52

> <JCHEM_AVERAGE_POLARIZABILITY>
36.57828569566354

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(9Z,11Z)-octadeca-9,11-dienoic acid

> <ALOGPS_LOGP>
7.11

> <JCHEM_LOGP>
6.421876794333333

> <ALOGPS_LOGS>
-6.28

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.988167283903808

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
88.51879999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.48e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(9Z,11Z)-octadeca-9,11-dienoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-NOV-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-NOV-15         0                                  
HETATM    1  C   UNK     0      -6.407   7.081   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.073   6.311   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.739   7.081   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.406   6.311   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.072   7.081   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.262   6.311   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.595   7.081   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.929   6.311   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.929   4.771   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.263   4.001   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.596   4.771   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.930   4.001   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.264   4.771   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.597   4.001   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.931   4.771   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.265   4.001   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      13.598   4.771   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      14.932   4.001   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      16.266   4.771   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      14.932   2.461   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   38    0
END

View in JSmol

Synonyms

Value	Source
Ricinenate	Generator
9,11-Linoleic acid, (e,Z)-isomer	MeSH
9-cis-11-trans-Octadecadienoic acid	MeSH
cis-9-trans-11-Octadecadienoic acid	MeSH
Rumenic acid	MeSH
9,11-Linoleic acid, potassium salt	MeSH
9,11-Octadecadienoic acid	MeSH
9,11-Linoleic acid, (Z,e)-isomer	MeSH
c9t11 CLA	MeSH
(9Z,11E)-9,11-Octadecadienoic acid	MeSH
9,11-Isolinoleic acid	MeSH
9,11-Linoleic acid, (e,e)-isomer	MeSH
9,11-Octadecadienoate	MeSH
Octadeca-9,11-dienoic acid	MeSH
9,11-Linoleic acid	MeSH
9,11-Linoleic acid, (Z,Z)-isomer	MeSH

Chemical Formula

C₁₈H₃₂O₂

Average Mass

280.4520 Da

Monoisotopic Mass

280.24023 Da

IUPAC Name

(9Z,11Z)-octadeca-9,11-dienoic acid

Traditional Name

(9Z,11Z)-octadeca-9,11-dienoic acid

CAS Registry Number

Not Available

SMILES

CCCCCC\C=C/C=C\CCCCCCCC(O)=O

InChI Identifier

InChI=1S/C18H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h7-10H,2-6,11-17H2,1H3,(H,19,20)/b8-7-,10-9-

InChI Key

JBYXPOFIGCOSSB-QRLRYFCNSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Carthamus oxyacanthus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as lineolic acids and derivatives. These are derivatives of lineolic acid. Lineolic acid is a polyunsaturated omega-6 18 carbon long fatty acid, with two CC double bonds at the 9- and 12-positions.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Lineolic acids and derivatives

Direct Parent

Lineolic acids and derivatives

Alternative Parents

Substituents

Octadecanoid
Long-chain fatty acid
Fatty acid
Unsaturated fatty acid
Straight chain 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 Framework

Aliphatic acyclic compounds

External Descriptors

Unsaturated fatty acids (LMFA01030117 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	7.11	ALOGPS
logP	6.42	ChemAxon
logS	-6.3	ALOGPS
pKa (Strongest Acidic)	4.99	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	88.52 m³·mol⁻¹	ChemAxon
Polarizability	36.58 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5282795

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (9z,11z)-octadeca-9,11-dienoic acid (NP0244931)

MOL for NP0244931 ((9z,11z)-octadeca-9,11-dienoic acid)

3D MOL for NP0244931 ((9z,11z)-octadeca-9,11-dienoic acid)

3D SDF for NP0244931 ((9z,11z)-octadeca-9,11-dienoic acid)

3D-SDF for NP0244931 ((9z,11z)-octadeca-9,11-dienoic acid)

PDB for NP0244931 ((9z,11z)-octadeca-9,11-dienoic acid)

3D PDB for NP0244931 ((9z,11z)-octadeca-9,11-dienoic acid)

SMILES for NP0244931 ((9z,11z)-octadeca-9,11-dienoic acid)

INCHI for NP0244931 ((9z,11z)-octadeca-9,11-dienoic acid)

Structure for NP0244931 ((9z,11z)-octadeca-9,11-dienoic acid)

3D Structure for NP0244931 ((9z,11z)-octadeca-9,11-dienoic acid)