NP-MRD: Showing NP-Card for Benzyl acetate (NP0001429)

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Record Information

Version

2.0

Created at

2012-09-11 17:42:15 UTC

Updated at

2021-08-19 23:59:08 UTC

NP-MRD ID

NP0001429

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Benzyl acetate

Description

Benzyl acetate, also known as benzyl ethanoate or fema 2135, belongs to the class of organic compounds known as benzyloxycarbonyls. These are organic compounds containing a carbonyl group substituted with a benzyloxyl group. Benzyl acetate is a sweet, apple, and apricot tasting compound. Benzyl acetate is found, on average, in the highest concentration within sweet basils. Benzyl acetate has also been detected, but not quantified, in several different foods, such as figs, fruits, pomes, tea, and alcoholic beverages. On high concnetrations benzyl acetate is a potentially toxic compound. If the compound has entered the eyes, they should be washed with large quantities of isotonic saline or water.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv1652306242117433D          

 21 21  0  0  0  0            999 V2000
    3.4770    0.3872   -1.0375 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2264    0.5277   -0.2485 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5083    1.5282   -0.5004 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7971   -0.3326    0.7188 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6445   -0.2593    1.4890 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6251   -0.2726    0.7258 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2289   -1.4168    0.2435 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4147   -1.3758   -0.4591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0505   -0.1800   -0.7103 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4627    0.9717   -0.2368 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2741    0.9062    0.4649 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4238    0.9540   -1.9760 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7634   -0.6731   -1.1813 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2820    0.8674   -0.4237 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6650    0.5897    2.2304 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6338   -1.1775    2.1478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7131   -2.3554    0.4508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8587   -2.2993   -0.8224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9856   -0.1624   -1.2661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9339    1.9243   -0.4159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8741    1.8486    0.8070 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11  6  1  0  0  0  0
  1 12  1  0  0  0  0
  1 13  1  0  0  0  0
  1 14  1  0  0  0  0
  5 15  1  0  0  0  0
  5 16  1  0  0  0  0
  7 17  1  0  0  0  0
  8 18  1  0  0  0  0
  9 19  1  0  0  0  0
 10 20  1  0  0  0  0
 11 21  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0001429

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])OC(=O)C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C9H10O2/c1-8(10)11-7-9-5-3-2-4-6-9/h2-6H,7H2,1H3

> <INCHI_KEY>
QUKGYYKBILRGFE-UHFFFAOYSA-N

> <FORMULA>
C9H10O2

> <MOLECULAR_WEIGHT>
150.1745

> <EXACT_MASS>
150.068079564

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
21

> <JCHEM_AVERAGE_POLARIZABILITY>
16.032454846971223

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
benzyl acetate

> <ALOGPS_LOGP>
2.07

> <JCHEM_LOGP>
1.6470214589999999

> <ALOGPS_LOGS>
-2.46

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.005728626239905

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
42.025400000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.20e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
benzyl acetate

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 24-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-JUN-21         0                                  
HETATM    1  C   UNK     0       3.477   0.387  -1.038  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.226   0.528  -0.249  0.00  0.00           C+0
HETATM    3  O   UNK     0       1.508   1.528  -0.500  0.00  0.00           O+0
HETATM    4  O   UNK     0       1.797  -0.333   0.719  0.00  0.00           O+0
HETATM    5  C   UNK     0       0.645  -0.259   1.489  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.625  -0.273   0.726  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.229  -1.417   0.244  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.415  -1.376  -0.459  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.050  -0.180  -0.710  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.463   0.972  -0.237  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.274   0.906   0.465  0.00  0.00           C+0
HETATM   12  H   UNK     0       3.424   0.954  -1.976  0.00  0.00           H+0
HETATM   13  H   UNK     0       3.763  -0.673  -1.181  0.00  0.00           H+0
HETATM   14  H   UNK     0       4.282   0.867  -0.424  0.00  0.00           H+0
HETATM   15  H   UNK     0       0.665   0.590   2.230  0.00  0.00           H+0
HETATM   16  H   UNK     0       0.634  -1.178   2.148  0.00  0.00           H+0
HETATM   17  H   UNK     0      -0.713  -2.355   0.451  0.00  0.00           H+0
HETATM   18  H   UNK     0      -2.859  -2.299  -0.822  0.00  0.00           H+0
HETATM   19  H   UNK     0      -3.986  -0.162  -1.266  0.00  0.00           H+0
HETATM   20  H   UNK     0      -2.934   1.924  -0.416  0.00  0.00           H+0
HETATM   21  H   UNK     0      -0.874   1.849   0.807  0.00  0.00           H+0
CONECT    1    2   12   13   14                                             
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   15   16                                             
CONECT    6    5    7   11                                                  
CONECT    7    6    8   17                                                  
CONECT    8    7    9   18                                                  
CONECT    9    8   10   19                                                  
CONECT   10    9   11   20                                                  
CONECT   11   10    6   21                                                  
CONECT   12    1                                                            
CONECT   13    1                                                            
CONECT   14    1                                                            
CONECT   15    5                                                            
CONECT   16    5                                                            
CONECT   17    7                                                            
CONECT   18    8                                                            
CONECT   19    9                                                            
CONECT   20   10                                                            
CONECT   21   11                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   42    0
END

View in JSmol

Synonyms

Value	Source
Acetic acid, benzyl ester	ChEBI
Acetic acid, phenylmethyl ester	ChEBI
Benzyl ethanoate	ChEBI
Phenylmethyl ethanoate	ChEBI
Acetate, benzyl ester	Generator
Acetate, phenylmethyl ester	Generator
Benzyl ethanoic acid	Generator
Phenylmethyl ethanoic acid	Generator
Benzyl acetic acid	Generator
(Acetoxymethyl)benzene	HMDB
Acetato de bencilo	HMDB
Acetic acid benzyl ester	HMDB
Acetic acid phenylmethyl ester	HMDB
alpha-Acetoxytoluene	HMDB
Benzyl acetate + glycine combination	HMDB
Benzyl ester OF acetic acid	HMDB
Benzylester kyseliny octove	HMDB
FEMA 2135	HMDB
Nchem.167-comp5	HMDB
Phenylmethyl acetate	HMDB
Plastolin I	HMDB
(14C)Benzyl acetate	HMDB
Benzyl (1-14C)acetate	HMDB
Benzyl (2-14C)acetate	HMDB

Chemical Formula

C₉H₁₀O₂

Average Mass

150.1745 Da

Monoisotopic Mass

150.06808 Da

IUPAC Name

benzyl acetate

Traditional Name

benzyl acetate

CAS Registry Number

140-11-4

SMILES

[H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])OC(=O)C([H])([H])[H]

InChI Identifier

InChI=1S/C9H10O2/c1-8(10)11-7-9-5-3-2-4-6-9/h2-6H,7H2,1H3

InChI Key

QUKGYYKBILRGFE-UHFFFAOYSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Antidesma laciniatum	LOTUS Database	35616633
Cananga odorata	LOTUS Database	35616633
Cannabis sativa	CannabisDB	Not Available
Cinnamomum verum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Cucumis melo	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Curio articulatus	LOTUS Database	35616633
Daphne odora	LOTUS Database	35616633
Ficus carica	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Hesperis matronalis	LOTUS Database	35616633
Jasminum grandiflorum	Plant	KNApSAcK
Malus domestica	LOTUS Database	35616633
Malus pumila	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Mandragora autumnalis	KNApSAcK Database	22123792
Mandragora officinarum	LOTUS Database	35616633
Narcissus tazetta	LOTUS Database	35616633
Ocimum basilicum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Pandanus tectorius	LOTUS Database	35616633
Prunus persica	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Prunus yedoensis	LOTUS Database	35616633
Solanum quitoense	KNApSAcK Database	22123792
Spathiphyllum cannifolium	LOTUS Database	35616633
Spondias mombin	LOTUS Database	35616633
Syzygium aromaticum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Tanacetum parthenium	LOTUS Database	35616633
Tricholoma matsutake	LOTUS Database	35616633
Vaccinium vitis-idaea	LOTUS Database	35616633
Vitis rotundifolia	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzyloxycarbonyls. These are organic compounds containing a carbonyl group substituted with a benzyloxyl group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzyloxycarbonyls

Direct Parent

Benzyloxycarbonyls

Alternative Parents

Substituents

Benzyloxycarbonyl
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

acetate ester (CHEBI:52051 )
a small molecule (CPD-6501 )

Physical Properties

State

Liquid

Experimental Properties

Property	Value	Reference
Melting Point	-51.3 °C	Not Available
Boiling Point	212.00 to 215.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	3.1 mg/mL at 25 °C	Not Available
LogP	1.96	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.52 g/L	ALOGPS
logP	2.07	ALOGPS
logP	1.65	ChemAxon
logS	-2.5	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	3	ChemAxon
Refractivity	42.03 m³·mol⁻¹	ChemAxon
Polarizability	16.03 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0031310

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Benzyl acetate

METLIN ID

Not Available

PubChem Compound

PDB ID

ChEBI ID

Good Scents ID

References

General References

Lotsch J, Ultsch A, Hahner A, Willgeroth V, Bensafi M, Zaliani A, Hummel T: Data-science based analysis of perceptual spaces of odors in olfactory loss. Sci Rep. 2021 May 19;11(1):10595. doi: 10.1038/s41598-021-89969-9. [PubMed:34012047 ]
Nakanishi S, Makita M, Denda M: Effects of trans-2-nonenal and olfactory masking odorants on proliferation of human keratinocytes. Biochem Biophys Res Commun. 2021 Apr 9;548:1-6. doi: 10.1016/j.bbrc.2021.02.050. Epub 2021 Feb 22. [PubMed:33631667 ]
Terry MI, Ruiz-Hernandez V, Aguila DJ, Weiss J, Egea-Cortines M: The Effect of Post-harvest Conditions in Narcissus sp. Cut Flowers Scent Profile. Front Plant Sci. 2021 Jan 7;11:540821. doi: 10.3389/fpls.2020.540821. eCollection 2020. [PubMed:33488635 ]
Upadhyay N, Singh VK, Dwivedy AK, Chaudhari AK, Dubey NK: Assessment of nanoencapsulated Cananga odorata essential oil in chitosan nanopolymer as a green approach to boost the antifungal, antioxidant and in situ efficacy. Int J Biol Macromol. 2021 Feb 28;171:480-490. doi: 10.1016/j.ijbiomac.2021.01.024. Epub 2021 Jan 9. [PubMed:33428956 ]
Bao F, Zhang T, Ding A, Ding A, Yang W, Wang J, Cheng T, Zhang Q: Metabolic, Enzymatic Activity, and Transcriptomic Analysis Reveals the Mechanism Underlying the Lack of Characteristic Floral Scent in Apricot Mei Varieties. Front Plant Sci. 2020 Oct 22;11:574982. doi: 10.3389/fpls.2020.574982. eCollection 2020. [PubMed:33193512 ]
Akkarasereenon K, Tangdenpaisal K, Ruchirawat S, Ploypradith P: Chemoselective acid-catalyzed [4 + 2]-cycloaddition reactions of ortho-quinone methides and styrenes/stilbenes/cinnamates. Org Biomol Chem. 2020 Nov 12;18(43):8854-8866. doi: 10.1039/d0ob01312a. [PubMed:33179702 ]
Fang F, Oliva M, Ovadia R, Bar E, Nissim-Levi A, Kumar V, Wang R, Neeman A, Zaccai M, Lewinsohn E, Oren-Shamir M: Increased substrate availability reveals the potential of scentless lisianthus flowers in producing fragrant benzenoid-phenylpropanoids. Physiol Plant. 2021 May;172(1):19-28. doi: 10.1111/ppl.13264. Epub 2020 Dec 27. [PubMed:33161590 ]
Du Y, Zhou A, Chen J: Olfactory and behavioral responses to acetate esters in red imported fire ant, Solenopsis invicta. Pest Manag Sci. 2021 Mar;77(3):1371-1382. doi: 10.1002/ps.6152. Epub 2020 Nov 16. [PubMed:33089649 ]
Wang J, Zhu Y, Shi J, Yan H, Wang M, Ma W, Zhang Y, Peng Q, Chen Y, Lin Z: Discrimination and Identification of Aroma Profiles and Characterized Odorants in Citrus Blend Black Tea with Different Citrus Species. Molecules. 2020 Sep 14;25(18). pii: molecules25184208. doi: 10.3390/molecules25184208. [PubMed:32937894 ]
Chen JH, Xiang W, Cao KX, Lu X, Yao SC, Hung D, Huang RS, Li LB: Characterization of Volatile Organic Compounds Emitted from Endophytic Burkholderia cenocepacia ETR-B22 by SPME-GC-MS and Their Inhibitory Activity against Various Plant Fungal Pathogens. Molecules. 2020 Aug 19;25(17). pii: molecules25173765. doi: 10.3390/molecules25173765. [PubMed:32824884 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing NP-Card for Benzyl acetate (NP0001429)

MOL for NP0001429 (Benzyl acetate)

3D MOL for NP0001429 (Benzyl acetate)

3D SDF for NP0001429 (Benzyl acetate)

3D-SDF for NP0001429 (Benzyl acetate)

PDB for NP0001429 (Benzyl acetate)

3D PDB for NP0001429 (Benzyl acetate)

SMILES for NP0001429 (Benzyl acetate)

INCHI for NP0001429 (Benzyl acetate)

Structure for NP0001429 (Benzyl acetate)

3D Structure for NP0001429 (Benzyl acetate)