NP-MRD: Showing NP-Card for Piperic acid (NP0047738)

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Record Information

Version

2.0

Created at

2022-03-17 20:45:08 UTC

Updated at

2022-03-17 20:45:08 UTC

NP-MRD ID

NP0047738

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Piperic acid

Description

Piperic acid, also known as piperate, belongs to the class of organic compounds known as benzodioxoles. These are organic compounds containing a benzene ring fused to either isomers of dioxole. Dioxole is a five-membered unsaturated ring of two oxygen atoms and three carbon atoms. On reduction with sodium amalgam piperic acid forms α- and β-dihydropiperic acid, C12H12O4, and the latter can take up two further atoms of hydrogen to produce tetrahydropiperic acid. Piperic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Piperic acid has been detected, but not quantified in, herbs and spices and pepper (spice). This could make piperic acid a potential biomarker for the consumption of these foods. Piperonal has many uses in industry and is itself a precursor to a good subsection of other chemicals. Piperic acid is an intermediate in the synthesis of other compounds such as piperonal, and as-such may be used to produce fragrances, perfumes flavorants and drugs as well as other useful compounds. Reaction of piperic acid with strong oxidizers such as potassium permanganate or ozone, or a halogen such as bromine followed by sodium hydroxide causes oxidative cleavage of the double-bonds, yielding piperonal and piperonylic acid. Piperic acid is a chemical often obtained by the base-hydrolysis of the alkaloid piperine from black pepper, followed by acidification of the corresponding salt. The toxic compound piperidine is given off during the base-hydrolysis of piperine and as-such, safety precautions should be taken. Piperic acid is found in Mentha piperita , Minthostachys verticillata and Piper tuberculatum. Piperic acid can be prepared from the commercially-available alkaloid piperine, a cyclic amide containing a piperidine group, by reacting it with a hydroxide such as potassium hydroxide, then acidifying the formed piperate salt with hydrochloric acid or another acid.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061307212D          

 16 17  0  0  0  0            999 V2000
    5.4223    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7079   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1368    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2789   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2949    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9934    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5645    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1368    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4223    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8513    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798    1.0799    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7798   -0.2549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  1  2  0  0  0  0
  4  2  2  0  0  0  0
  6  5  2  0  0  0  0
  9  3  1  0  0  0  0
  9  5  1  0  0  0  0
  9  7  2  0  0  0  0
 10  6  1  0  0  0  0
 11  7  1  0  0  0  0
 11 10  2  0  0  0  0
 12  4  1  0  0  0  0
 13 12  2  0  0  0  0
 14 12  1  0  0  0  0
 15  8  1  0  0  0  0
 15 10  1  0  0  0  0
 16  8  1  0  0  0  0
 16 11  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0047738

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(=O)\C=C\C=C/C1=CC2=C(OCO2)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C12H10O4/c13-12(14)4-2-1-3-9-5-6-10-11(7-9)16-8-15-10/h1-7H,8H2,(H,13,14)/b3-1-,4-2+

> <INCHI_KEY>
RHBGITBPARBDPH-HSFFGMMNSA-N

> <FORMULA>
C12H10O4

> <MOLECULAR_WEIGHT>
218.2054

> <EXACT_MASS>
218.057908808

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
21.474786156036856

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E,4Z)-5-(2H-1,3-benzodioxol-5-yl)penta-2,4-dienoic acid

> <ALOGPS_LOGP>
2.79

> <JCHEM_LOGP>
2.286535400999999

> <ALOGPS_LOGS>
-2.84

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.816675999041073

> <JCHEM_PKA_STRONGEST_BASIC>
-4.741141031886499

> <JCHEM_POLAR_SURFACE_AREA>
55.760000000000005

> <JCHEM_REFRACTIVITY>
59.14540000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.13e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E,4Z)-5-(2H-1,3-benzodioxol-5-yl)penta-2,4-dienoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      10.122   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.122   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.788  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.455   2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.454   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.121   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.121  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.417   0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.454   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.787   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.787   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      11.455   3.850   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      10.122   4.620   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      12.789   4.620   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       3.322   2.016   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       3.322  -0.476   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    9                                                       
CONECT    4    2   12                                                       
CONECT    5    6    9                                                       
CONECT    6    5   10                                                       
CONECT    7    9   11                                                       
CONECT    8   15   16                                                       
CONECT    9    3    5    7                                                  
CONECT   10    6   11   15                                                  
CONECT   11    7   10   16                                                  
CONECT   12    4   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15    8   10                                                       
CONECT   16    8   11                                                       
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

View in JSmol

Synonyms

Value	Source
Piperate	Generator
2,4-Pentadienoic acid, 5-(1,3-benzodioxol-5-yl)- (9ci)	HMDB
5-(1,3-Benzenedioxol-5-yl)-2,4-pentadienoic acid, 9ci	HMDB
5-(1,3-Benzodioxol-5-yl)-2,4-pentadienoic acid	HMDB
5-(1,3-Benzodioxol-5-yl)penta-2,4-dienoic acid	HMDB
Piperic acid (8ci)	HMDB
Piperic acid, 8ci	HMDB
Piperinic acid	HMDB
Piperonic acid	HMDB
(2E,4Z)-5-(2H-1,3-Benzodioxol-5-yl)penta-2,4-dienoate	Generator

Chemical Formula

C₁₂H₁₀O₄

Average Mass

218.2054 Da

Monoisotopic Mass

218.05791 Da

IUPAC Name

(2E,4Z)-5-(2H-1,3-benzodioxol-5-yl)penta-2,4-dienoic acid

Traditional Name

(2E,4Z)-5-(2H-1,3-benzodioxol-5-yl)penta-2,4-dienoic acid

CAS Registry Number

5285-18-7

SMILES

OC(=O)\C=C\C=C/C1=CC2=C(OCO2)C=C1

InChI Identifier

InChI=1S/C12H10O4/c13-12(14)4-2-1-3-9-5-6-10-11(7-9)16-8-15-10/h1-7H,8H2,(H,13,14)/b3-1-,4-2+

InChI Key

RHBGITBPARBDPH-HSFFGMMNSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Mentha x piperita	Plant	KNApSAcK
Minthostachys verticillata	Plant	KNApSAcK
Piper nigrum L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Piper tuberculatum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzodioxoles. These are organic compounds containing a benzene ring fused to either isomers of dioxole. Dioxole is a five-membered unsaturated ring of two oxygen atoms and three carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzodioxoles

Sub Class

Not Available

Direct Parent

Benzodioxoles

Alternative Parents

Substituents

Benzodioxole
Styrene
Medium-chain fatty acid
Heterocyclic fatty acid
Unsaturated fatty acid
Benzenoid
Fatty acid
Fatty acyl
Acetal
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Oxacycle
Hydrocarbon derivative
Organooxygen compound
Organic oxide
Organic oxygen compound
Carbonyl group
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

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	2.79	ALOGPS
logP	2.29	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	3.82	ChemAxon
pKa (Strongest Basic)	-4.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	55.76 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	59.15 m³·mol⁻¹	ChemAxon
Polarizability	21.47 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0033779

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB011933

KNApSAcK ID

Not Available

Chemspider ID

22902400

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Piperic acid

METLIN ID

Not Available

PubChem Compound

13001421

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Piperic acid (NP0047738)

MOL for NP0047738 (Piperic acid)

3D MOL for NP0047738 (Piperic acid)

3D SDF for NP0047738 (Piperic acid)

3D-SDF for NP0047738 (Piperic acid)

PDB for NP0047738 (Piperic acid)

3D PDB for NP0047738 (Piperic acid)

SMILES for NP0047738 (Piperic acid)

INCHI for NP0047738 (Piperic acid)

Structure for NP0047738 (Piperic acid)

3D Structure for NP0047738 (Piperic acid)