NP-MRD: Showing NP-Card for Citronellyl butyrate (NP0048709)

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Record Information

Version

2.0

Created at

2022-03-17 21:00:57 UTC

Updated at

2022-03-17 21:00:57 UTC

NP-MRD ID

NP0048709

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Citronellyl butyrate

Description

Citronellyl butyrate, also known as E275 or fema 2312, belongs to the class of organic compounds known as fatty alcohol esters. These are ester derivatives of a fatty alcohol. Citronellyl butyrate is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Citronellyl butyrate is a sweet, floral, and fruity tasting compound. Outside of the human body, Citronellyl butyrate has been detected, but not quantified in, several different foods, such as citrus, fruits, garden tomato, and herbs and spices. Citronellyl butyrate is found in Caiman crocodilus, Cryptomeria japonica, Origanum syriacum and Pelargonium quercifolium. This could make citronellyl butyrate a potential biomarker for the consumption of these foods.

Structure

MOL SDF PDB SMILES InChI

  Mrv0541 05061309392D          

 16 15  0  0  0  0            999 V2000
    1.3480   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9217   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2072   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3493   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7783   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4927   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0638   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6349   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9204   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2072   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3493   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4914   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4914   -1.5395    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2059   -0.3020    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  1  1  0  0  0  0
  7  5  1  0  0  0  0
  8  6  1  0  0  0  0
  9  6  1  0  0  0  0
 11 10  1  0  0  0  0
 12  2  1  0  0  0  0
 12  3  1  0  0  0  0
 12  8  2  0  0  0  0
 13  4  1  0  0  0  0
 13  9  1  0  0  0  0
 13 10  1  0  0  0  0
 14  7  1  0  0  0  0
 15 14  2  0  0  0  0
 16 11  1  0  0  0  0
 16 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0048709

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C14H26O2/c1-5-7-14(15)16-11-10-13(4)9-6-8-12(2)3/h8,13H,5-7,9-11H2,1-4H3

> <INCHI_KEY>
XQPZQXTWYZAXAK-UHFFFAOYSA-N

> <FORMULA>
C14H26O2

> <MOLECULAR_WEIGHT>
226.355

> <EXACT_MASS>
226.193280076

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
28.22763795913702

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
4.93

> <JCHEM_LOGP>
4.338285239666666

> <ALOGPS_LOGS>
-4.29

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.032639712781787

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
68.8655

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.17e-02 g/l

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

> <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       2.516  -0.564   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      18.521  -0.564   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      17.187  -2.874   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.852  -2.874   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.850  -1.334   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      14.519  -1.334   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.184  -0.564   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      15.853  -0.564   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      13.186  -0.564   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.518  -0.564   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.185  -1.334   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      17.187  -1.334   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      11.852  -1.334   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.517  -1.334   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       6.517  -2.874   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       7.851  -0.564   0.000  0.00  0.00           O+0
CONECT    1    5                                                            
CONECT    2   12                                                            
CONECT    3   12                                                            
CONECT    4   13                                                            
CONECT    5    1    7                                                       
CONECT    6    8    9                                                       
CONECT    7    5   14                                                       
CONECT    8    6   12                                                       
CONECT    9    6   13                                                       
CONECT   10   11   13                                                       
CONECT   11   10   16                                                       
CONECT   12    2    3    8                                                  
CONECT   13    4    9   10                                                  
CONECT   14    7   15   16                                                  
CONECT   15   14                                                            
CONECT   16   11   14                                                       
MASTER        0    0    0    0    0    0    0    0   16    0   30    0
END

View in JSmol

Synonyms

Value	Source
Citronellyl butyric acid	Generator
(1)-3,7-Dimethyloct-6-enyl butyrate	HMDB
3,7-Dimethyl-6-octen-1-yl butyrate	HMDB
3,7-Dimethyl-6-octenyl butanoate	HMDB
Butanoic acid, 3,7-dimethyl-6-octen-1-yl ester	HMDB
Butanoic acid, 3,7-dimethyl-6-octenyl ester	HMDB
Butyric acid, 3,7-dimethyl-6-octenyl ester (8ci)	HMDB
Butyric acid, ester with citronellol	HMDB
e275	HMDB
FEMA 2312	HMDB

Chemical Formula

C₁₄H₂₆O₂

Average Mass

226.3550 Da

Monoisotopic Mass

226.19328 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

141-16-2

SMILES

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

InChI Identifier

InChI=1S/C14H26O2/c1-5-7-14(15)16-11-10-13(4)9-6-8-12(2)3/h8,13H,5-7,9-11H2,1-4H3

InChI Key

XQPZQXTWYZAXAK-UHFFFAOYSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Caiman crocodilus	LOTUS Database	35616633
Cryptomeria japonica	LOTUS Database	35616633
Origanum syriacum	LOTUS Database	35616633
Pelargonium quercifolium	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
Fatty acid ester
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	4.93	ALOGPS
logP	4.34	ChemAxon
logS	-4.3	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	9	ChemAxon
Refractivity	68.87 m³·mol⁻¹	ChemAxon
Polarizability	28.23 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

HMDB0037227

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB016234

KNApSAcK ID

Not Available

Chemspider ID

8503

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

8835

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Citronellyl butyrate (NP0048709)

MOL for NP0048709 (Citronellyl butyrate)

3D MOL for NP0048709 (Citronellyl butyrate)

3D SDF for NP0048709 (Citronellyl butyrate)

3D-SDF for NP0048709 (Citronellyl butyrate)

PDB for NP0048709 (Citronellyl butyrate)

3D PDB for NP0048709 (Citronellyl butyrate)

SMILES for NP0048709 (Citronellyl butyrate)

INCHI for NP0048709 (Citronellyl butyrate)

Structure for NP0048709 (Citronellyl butyrate)

3D Structure for NP0048709 (Citronellyl butyrate)