NP-MRD: Showing NP-Card for Citronellyl propionate (NP0048708)

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Record Information

Version

2.0

Created at

2022-03-17 21:00:56 UTC

Updated at

2022-03-17 21:00:56 UTC

NP-MRD ID

NP0048708

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Citronellyl propionate

Description

Citronellyl propionate, also known as E410 or fema 2316, belongs to the class of organic compounds known as fatty alcohol esters. These are ester derivatives of a fatty alcohol. Citronellyl propionate is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Citronellyl propionate is a bitter, floral, and fruity tasting compound. Outside of the human body, Citronellyl propionate has been detected, but not quantified in, garden tomato. Citronellyl propionate is found in Artemisia monosperma, Cryptomeria japonica, Pelargonium quercifolium, Pinus heldreichii and Saussurea costus. This could make citronellyl propionate a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI

  Mrv0541 05061309392D          

 15 14  0  0  0  0            999 V2000
   -0.6039    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2552    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5408   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6829   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1118    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8263    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3974    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9684    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5408    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6829    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250   -0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0  0  0  0
  7  6  1  0  0  0  0
  8  6  1  0  0  0  0
 10  9  1  0  0  0  0
 11  2  1  0  0  0  0
 11  3  1  0  0  0  0
 11  7  2  0  0  0  0
 12  4  1  0  0  0  0
 12  8  1  0  0  0  0
 12  9  1  0  0  0  0
 13  5  1  0  0  0  0
 14 13  2  0  0  0  0
 15 10  1  0  0  0  0
 15 13  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0048708

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC(=O)OCCC(C)CCC=C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C13H24O2/c1-5-13(14)15-10-9-12(4)8-6-7-11(2)3/h7,12H,5-6,8-10H2,1-4H3

> <INCHI_KEY>
POPNTVRHTZDEBW-UHFFFAOYSA-N

> <FORMULA>
C13H24O2

> <MOLECULAR_WEIGHT>
212.3285

> <EXACT_MASS>
212.177630012

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
26.470527258048612

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,7-dimethyloct-6-en-1-yl propanoate

> <ALOGPS_LOGP>
4.54

> <JCHEM_LOGP>
3.8937165746666658

> <ALOGPS_LOGS>
-3.87

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.029696556762688

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
64.26450000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.85e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,7-dimethyloct-6-en-1-yl propanoate

> <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      -1.127   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      13.543   0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      12.209  -1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.875  -1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.206   0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.542   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.876   0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.208   0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.541   0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.207   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      12.209   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.875   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       1.540  -1.540   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       2.874   0.770   0.000  0.00  0.00           O+0
CONECT    1    5                                                            
CONECT    2   11                                                            
CONECT    3   11                                                            
CONECT    4   12                                                            
CONECT    5    1   13                                                       
CONECT    6    7    8                                                       
CONECT    7    6   11                                                       
CONECT    8    6   12                                                       
CONECT    9   10   12                                                       
CONECT   10    9   15                                                       
CONECT   11    2    3    7                                                  
CONECT   12    4    8    9                                                  
CONECT   13    5   14   15                                                  
CONECT   14   13                                                            
CONECT   15   10   13                                                       
MASTER        0    0    0    0    0    0    0    0   15    0   28    0
END

View in JSmol

Synonyms

Value	Source
Citronellyl propionic acid	Generator
(+)-3,7-Dimethyloct-6-enyl propionate	HMDB
(1)-3,7-Dimethyloct-6-enyl propionate	HMDB
3,7-Dimethyl-6-octen-1-ol propanoate	HMDB
3,7-Dimethyl-6-octen-1-yl propanoate	HMDB
3,7-Dimethyl-6-octen-1-yl propionate	HMDB
3,7-Dimethyl-6-octenyl propionate	HMDB
6-Octen-1-ol, 3,7-dimethyl-, 1-propanoate	HMDB
6-Octen-1-ol, 3,7-dimethyl-, propanoate	HMDB
6-Octen-1-ol, 3,7-dimethyl-, propionate	HMDB
6-Octen-1-ol, 3,7-dimethyl-, propionate (7ci,8ci)	HMDB
Citronellyl N-proprionate	HMDB
Citronellyl propanoate	HMDB
Citronellyl propianoate	HMDB
e410	HMDB
FEMA 2316	HMDB
Methyl diphenylphosphite	HMDB
Propionic acid, ester with citronellol	HMDB
Propionic acid, ester with citronellol (6ci)	HMDB

Chemical Formula

C₁₃H₂₄O₂

Average Mass

212.3285 Da

Monoisotopic Mass

212.17763 Da

IUPAC Name

3,7-dimethyloct-6-en-1-yl propanoate

Traditional Name

3,7-dimethyloct-6-en-1-yl propanoate

CAS Registry Number

141-14-0

SMILES

CCC(=O)OCCC(C)CCC=C(C)C

InChI Identifier

InChI=1S/C13H24O2/c1-5-13(14)15-10-9-12(4)8-6-7-11(2)3/h7,12H,5-6,8-10H2,1-4H3

InChI Key

POPNTVRHTZDEBW-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Artemisia monosperma	LOTUS Database	35616633
Cryptomeria japonica	LOTUS Database	35616633
Pelargonium quercifolium	LOTUS Database	35616633
Pinus heldreichii	LOTUS Database	35616633
Saussurea costus	LOTUS Database	35616633
Solanum lycopersicum	FooDB	Shmuel Yannai Dictionary of Food Compounds with CD-ROM: Additives, Flavors, and Ingredients. Chap...

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as fatty alcohol esters. These are ester derivatives of a fatty alcohol.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty alcohol esters

Direct Parent

Fatty alcohol esters

Alternative Parents

Substituents

Fatty alcohol ester
Monoterpenoid
Acyclic monoterpenoid
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic 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	4.54	ALOGPS
logP	3.89	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.3 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	64.26 m³·mol⁻¹	ChemAxon
Polarizability	26.47 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0037226

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB016233

KNApSAcK ID

Not Available

Chemspider ID

8502

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

8834

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Citronellyl propionate (NP0048708)

MOL for NP0048708 (Citronellyl propionate)

3D MOL for NP0048708 (Citronellyl propionate)

3D SDF for NP0048708 (Citronellyl propionate)

3D-SDF for NP0048708 (Citronellyl propionate)

PDB for NP0048708 (Citronellyl propionate)

3D PDB for NP0048708 (Citronellyl propionate)

SMILES for NP0048708 (Citronellyl propionate)

INCHI for NP0048708 (Citronellyl propionate)

Structure for NP0048708 (Citronellyl propionate)

3D Structure for NP0048708 (Citronellyl propionate)