NP-MRD: Showing NP-Card for citronellyl formate (NP0286971)

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Record Information

Version

2.0

Created at

2022-09-09 15:48:09 UTC

Updated at

2022-09-09 15:48:09 UTC

NP-MRD ID

NP0286971

Secondary Accession Numbers

None

Natural Product Identification

Common Name

citronellyl formate

Description

Citronellyl formate, also known as citronellyl methanoate or fema 2314, belongs to the class of organic compounds known as fatty alcohol esters. These are ester derivatives of a fatty alcohol. Citronellyl formate is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Citronellyl formate is an apricot, bergamot, and cucumber tasting compound. Outside of the human body, Citronellyl formate has been detected, but not quantified in, citrus and herbs and spices. citronellyl formate is found in Cryptomeria japonica, Daphne papyracea, Leptospermum scoparium, Pelargonium graveolens, Pelargonium quercifolium, Pelargonium vitifolium and Plectranthus glabratus. This could make citronellyl formate a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 33 32  0  0  0  0  0  0  0  0999 V2000
   -3.6314    1.5844   -1.2323 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4421    0.9370   -0.5327 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2367    1.3227    0.8724 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7163    0.1245   -1.2262 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5296   -0.6732   -0.9311 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0117   -0.6676    0.4448 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2677   -1.5148    0.5803 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8891   -2.9616    0.1795 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3983   -1.1185   -0.2930 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8755    0.2662    0.0308 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8449    1.1837   -0.1739 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0662    2.5180    0.0639 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1824    2.8958    0.4592 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3696    2.5877   -1.5998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9961    0.8909   -1.9974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4602    1.7106   -0.4937 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3905    2.0341    1.0234 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1244    1.9433    1.2509 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1786    0.4673    1.5522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0605   -0.0090   -2.3035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7897   -1.7281   -1.2639 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2730   -0.3841   -1.6823 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1204    0.2739    0.9406 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7428   -1.2575    1.0799 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5166   -1.5537    1.6542 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6966   -3.6206    0.5761 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9235   -3.0390   -0.9147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1028   -3.2238    0.5729 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1430   -1.1560   -1.3826 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2796   -1.8007   -0.1498 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2084    0.2401    1.1123 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7922    0.5046   -0.5547 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2821    3.2235   -0.0908 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  7  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
  7  6  1  0
  6  5  1  0
  5  4  1  0
  4  2  2  3
  2  1  1  0
  2  3  1  0
  8 26  1  0
  8 27  1  0
  8 28  1  0
  7 25  1  1
  9 29  1  0
  9 30  1  0
 10 31  1  0
 10 32  1  0
 12 33  1  0
  6 23  1  0
  6 24  1  0
  5 21  1  0
  5 22  1  0
  4 20  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  3 17  1  0
  3 18  1  0
  3 19  1  0
M  END

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      -8.057  -0.921   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.390  -0.921   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.723  -5.541   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.390  -4.001   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -6.724  -3.231   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.056  -3.231   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.389  -3.231   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.055  -4.001   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.612  -4.001   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -6.724  -1.691   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.723  -4.001   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       3.946  -3.231   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       1.278  -3.231   0.000  0.00  0.00           O+0
CONECT    1   10                                                            
CONECT    2   10                                                            
CONECT    3   11                                                            
CONECT    4    5    6                                                       
CONECT    5    4   10                                                       
CONECT    6    4   11                                                       
CONECT    7    8   11                                                       
CONECT    8    7   13                                                       
CONECT    9   12   13                                                       
CONECT   10    1    2    5                                                  
CONECT   11    3    6    7                                                  
CONECT   12    9                                                            
CONECT   13    8    9                                                       
MASTER        0    0    0    0    0    0    0    0   13    0   24    0
END

View in JSmol

Synonyms

Value	Source
Citronellyl formic acid	Generator
(+)-3,7-Dimethyloct-6-enyl formate	HMDB
(-)-3,7-Dimethyloct-6-enyl formate	HMDB
(1)-3,7-Dimethyloct-6-enyl formate	HMDB
2, 6-Dimethyl-2-octen-8-yl formate	HMDB
2,6-Dimethyl-2-octen-8-yl formate	HMDB
3,7-Dimethyl-6-octen-1-yl formate	HMDB
3,7-Dimethyl-6-octen-1-yl methanoate	HMDB
3,7-Dimethyl-6-octenyl formate	HMDB
6-Octen-1-ol, 3,7-dimethyl-, 1-formate	HMDB
6-Octen-1-ol, 3,7-dimethyl-, formate	HMDB
Citronellol formate	HMDB
Citronellol formate (6ci)	HMDB
Citronellyl methanoate	HMDB
Citronelyl formate	HMDB
FEMA 2314	HMDB
Formic acid, 3,7-dimethyl-6-octen-1-yl ester	HMDB
Formic acid, citronellyl ester	HMDB

Chemical Formula

C₁₁H₂₀O₂

Average Mass

184.2753 Da

Monoisotopic Mass

184.14633 Da

IUPAC Name

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

Traditional Name

citronellyl formate

CAS Registry Number

Not Available

SMILES

CC(CCOC=O)CCC=C(C)C

InChI Identifier

InChI=1S/C11H20O2/c1-10(2)5-4-6-11(3)7-8-13-9-12/h5,9,11H,4,6-8H2,1-3H3

InChI Key

DZNVIZQPWLDQHI-UHFFFAOYSA-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
Cryptomeria japonica	LOTUS Database	35616633
Daphne papyracea	LOTUS Database	35616633
Leptospermum scoparium	LOTUS Database	35616633
Pelargonium graveolens	LOTUS Database	35616633
Pelargonium quercifolium	LOTUS Database	35616633
Pelargonium vitifolium	LOTUS Database	35616633
Plectranthus glabratus	LOTUS Database	35616633

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

carboxylic ester (CHEBI:31406 )
Acyclic monoterpenoids (C12295 )
Acyclic monoterpenoids (LMPR0102010014 )

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	3.86	ALOGPS
logP	3.14	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Basic)	-6.8	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	7	ChemAxon
Refractivity	55.15 m³·mol⁻¹	ChemAxon
Polarizability	22.24 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

HMDB0033371

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

7778

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for citronellyl formate (NP0286971)

MOL for NP0286971 (citronellyl formate)

3D MOL for NP0286971 (citronellyl formate)

3D SDF for NP0286971 (citronellyl formate)

3D-SDF for NP0286971 (citronellyl formate)

PDB for NP0286971 (citronellyl formate)

3D PDB for NP0286971 (citronellyl formate)

SMILES for NP0286971 (citronellyl formate)

INCHI for NP0286971 (citronellyl formate)

Structure for NP0286971 (citronellyl formate)

3D Structure for NP0286971 (citronellyl formate)