NP-MRD: Showing NP-Card for Apiole (NP0047736)

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Record Information

Version

2.0

Created at

2022-03-17 20:45:05 UTC

Updated at

2022-03-17 20:45:06 UTC

NP-MRD ID

NP0047736

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Apiole

Description

Apiole, also known as apiol or camphre de persil, 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. According to a book called PIHKAL, Apiole had been used to synthesize a psychedelic amphetamine called DMMDA. In 1855 Joret and Homolle discovered that apiol was an effective treatment of amenorrea or lack of menstruation. In medicine it has been used, as essential oil or in purified form, for the treatment of menstrual disorders and as an abortifacient. The name apiole is also used for a closely related compound found in dill and in fennel roots, the positional isomer (dillapiole, 1-allyl-2,3-dimethoxy-4,5-methylenedioxybenzene. Apiole is an extremely weak basic (essentially neutral) compound (based on its pKa). Apiole is a faint and parsley tasting compound. Outside of the human body, Apiole is found, on average, in the highest concentration within parsley. Apiole has also been detected, but not quantified in, several different foods, such as fennels, dills, wild celeries, herbs and spices, and lovages. This could make apiole a potential biomarker for the consumption of these foods. No carcinogenicity was detected with parsley apiol or dill apiol in mice. Hippocrates wrote about parsley as an herb to cause an abortion. It is an irritant and, in high doses, it can cause liver and kidney damage. Apiole is found in Foeniculum vulgare , Asarum okinawense, Asarum petelotii, Brucea javanica, Chuquiraga spinosa, Cinnamomum camphora , Crithmum maritimum , Vincetoxicum hirundinaria, Daucus carota, Degeneria vitiensis, Heracleum pyrenaicum, Mosla cavaleriei, Nigella sativa L , Niphogeton dissecta, Ocimum gratissimum, Ocotea spp., Oenanthe javanica, Peperomia pellucida, Piper angustifolium, Piper artanthe, Piper brachystachyum, Piper lhotzkyanum, Piper marginatum , Piper mullesua, Piper regnellii , Piper schmidtii, Piper solmsianum, Sassafras albidum , Spatoglossum variabile, Stellaria pallida, Todaroa aurea and Zingiber cassumunar Roxb. . Plants containing apiole were used by women in the Middle Ages to terminate pregnancies.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 05061307212D          

 16 17  0  0  0  0            999 V2000
    4.7812    3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523   -0.5396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    3.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    3.1729    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0668    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378   -0.1271    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    3.1729    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  2  0  0  0  0
  5  4  1  0  0  0  0
  8  5  1  0  0  0  0
  8  6  2  0  0  0  0
  9  6  1  0  0  0  0
 10  8  1  0  0  0  0
 11  9  2  0  0  0  0
 12 10  2  0  0  0  0
 12 11  1  0  0  0  0
 13  2  1  0  0  0  0
 13  9  1  0  0  0  0
 14  3  1  0  0  0  0
 14 10  1  0  0  0  0
 15  7  1  0  0  0  0
 15 11  1  0  0  0  0
 16  7  1  0  0  0  0
 16 12  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0047736

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C2OCOC2=C(OC)C(CC=C)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C12H14O4/c1-4-5-8-6-9(13-2)11-12(10(8)14-3)16-7-15-11/h4,6H,1,5,7H2,2-3H3

> <INCHI_KEY>
QQRSPHJOOXUALR-UHFFFAOYSA-N

> <FORMULA>
C12H14O4

> <MOLECULAR_WEIGHT>
222.2372

> <EXACT_MASS>
222.089208936

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
22.87027944669294

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4,7-dimethoxy-5-(prop-2-en-1-yl)-2H-1,3-benzodioxole

> <ALOGPS_LOGP>
2.34

> <JCHEM_LOGP>
2.3797074853333333

> <ALOGPS_LOGS>
-2.55

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.39471840723923

> <JCHEM_POLAR_SURFACE_AREA>
36.92

> <JCHEM_REFRACTIVITY>
59.03860000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.33e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
apiol

> <JCHEM_VEBER_RULE>
1

$$$$

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       8.925   6.693   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.258  -1.007   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.590   6.693   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.591   5.923   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.591   4.383   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.258   3.613   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.924   1.303   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       4.924  -0.237   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       4.924   5.923   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       2.126   1.597   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       2.126   4.089   0.000  0.00  0.00           O+0
CONECT    1    4                                                            
CONECT    2   13                                                            
CONECT    3   14                                                            
CONECT    4    1    5                                                       
CONECT    5    4    8                                                       
CONECT    6    8    9                                                       
CONECT    7   15   16                                                       
CONECT    8    5    6   10                                                  
CONECT    9    6   11   13                                                  
CONECT   10    8   12   14                                                  
CONECT   11    9   12   15                                                  
CONECT   12   10   11   16                                                  
CONECT   13    2    9                                                       
CONECT   14    3   10                                                       
CONECT   15    7   11                                                       
CONECT   16    7   12                                                       
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

View in JSmol

Synonyms

Value	Source
1-Allyl-2,5-dimethoxy-3, 4-(methylenedioxy)benzene	HMDB
1-Allyl-2,5-dimethoxy-3,4-(methylenedioxy)-benzene	HMDB
1-Allyl-2,5-dimethoxy-3,4-(methylenedioxy)benzene	HMDB
1-Allyl-2,5-dimethoxy-3,4-methylenedioxybenzene	HMDB
4,7-Dimethoxy-5-(2-propen-1-yl)-1,3-benzodioxole	HMDB
4,7-Dimethoxy-5-(2-propenyl)-1,3-benzodioxole	HMDB
4,7-Dimethoxy-5-(2-propenyl)-1,3-benzodioxole, 9ci	HMDB
5-Allyl-4,7-dimethoxy-1,3-benzodioxol	HMDB
5-Allyl-4,7-dimethoxy-1,3-benzodioxole	HMDB
Apiol	HMDB
Apiole (parsley)	HMDB
Apioline	HMDB
Camphre de persil	HMDB
Parsley apiol	HMDB
Parsley apiole	HMDB
Parsley camphor	HMDB
Petersiliencampher	HMDB

Chemical Formula

C₁₂H₁₄O₄

Average Mass

222.2372 Da

Monoisotopic Mass

222.08921 Da

IUPAC Name

4,7-dimethoxy-5-(prop-2-en-1-yl)-2H-1,3-benzodioxole

Traditional Name

apiol

CAS Registry Number

523-80-8

SMILES

COC1=C2OCOC2=C(OC)C(CC=C)=C1

InChI Identifier

InChI=1S/C12H14O4/c1-4-5-8-6-9(13-2)11-12(10(8)14-3)16-7-15-11/h4,6H,1,5,7H2,2-3H3

InChI Key

QQRSPHJOOXUALR-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Anethum foeniculum	Plant	KNApSAcK
Anethum graveolens	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Apium graveolens	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Asarum okinawense	LOTUS Database	35616633
Asarum petelotii	LOTUS Database	35616633
Brucea javanica	LOTUS Database	35616633
Chuquiraga spinosa	LOTUS Database	35616633
Cinnamomum camphora	Plant	KNApSAcK
Crithmum maritimum	Plant	KNApSAcK
Cynanchum vincetoxicum	LOTUS Database	35616633
Daucus carota	LOTUS Database	35616633
Degeneria vitiensis	LOTUS Database	35616633
Foeniculum vulgare	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Heracleum pyrenaicum	Plant	KNApSAcK
Levisticum officinale	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Mosla cavaleriei	LOTUS Database	35616633
Nigella sativa L	Plant	KNApSAcK
Niphogeton dissecta	LOTUS Database	35616633
Ocimum gratissimum	LOTUS Database	35616633
Ocotea spp.	Plant	KNApSAcK
Oenanthe javanica	LOTUS Database	35616633
Peperomia pellucida	LOTUS Database	35616633
Petroselinum crispum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Piper angustifolium	Plant	KNApSAcK
Piper artanthe	LOTUS Database	35616633
Piper brachystachyum	Plant	KNApSAcK
Piper lhotzkyanum	Plant	KNApSAcK
Piper marginatum	Plant	KNApSAcK
Piper mullesua	LOTUS Database	35616633
Piper regnellii	Plant	KNApSAcK
Piper schmidtii	LOTUS Database	35616633
Piper solmsianum	Plant	KNApSAcK
Sassafras albidum	Plant	KNApSAcK
Spatoglossum variabile	Chromalveolata	KNApSAcK
Stellaria pallida	Plant	KNApSAcK
Todaroa aurea	LOTUS Database	35616633
Zingiber montanum	Plant	KNApSAcK

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
Anisole
Alkyl aryl ether
Benzenoid
Oxacycle
Ether
Acetal
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

benzodioxoles (CHEBI:70353 )

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	2.34	ALOGPS
logP	2.38	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	36.92 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	59.04 m³·mol⁻¹	ChemAxon
Polarizability	22.87 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon