NP-MRD: Showing NP-Card for Benzyl salicylate (NP0045464)

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Record Information

Version

2.0

Created at

2022-03-17 19:20:25 UTC

Updated at

2022-03-17 19:20:25 UTC

NP-MRD ID

NP0045464

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Benzyl salicylate

Description

Benzyl salicylate, also known as fema 2151, belongs to the class of organic compounds known as o-hydroxybenzoic acid esters. These are benzoic acid esters where the benzene ring is ortho-substituted with a hydroxy group. Benzyl salicylate is an extremely weak basic (essentially neutral) compound (based on its pKa). Trace impurities may have a significant influence on the odour. Benzyl salicylate is a sweet, balsam, and clean tasting compound. Outside of the human body, Benzyl salicylate has been detected, but not quantified in, cloves and herbs and spices. This could make benzyl salicylate a potential biomarker for the consumption of these foods. It occurs naturally in a variety of plants and plant extracts and is widely used in blends of fragrance materials. It is used as a solvent for crystalline synthetic musks and as a component and fixative in floral perfumes such as carnation, jasmine, lilac, and wallflower. Benzyl salicylate is a salicylic acid benzyl ester, a chemical compound most frequently used in cosmetics as a fragrance additive or UV light absorber. There is some evidence that people may become sensitized to this material and as a result, there is a restriction standard concerning the use of this material in fragrances by the International Fragrance Association. Benzyl salicylate is found in Aniba affinis, Aniba terminalis, Antidesma laciniatum, Cananga odorata , Cedronella canariensis, Daphne papyracea, Desmos chinensis, Dianthus caryophyllus , Erica manipuliflora, Acca sellowiana, Lophomyrtus bullata, Murraya paniculata , Nicotiana cavicola , Plumeria obtusa, Plumeria rubra, Polygala senega, Populus, Primula spp. and Uvaria grandiflora. It appears as an almost colorless liquid with a mild odor described as "very faint, sweet-floral, slightly balsamic" by those who can smell it, but many people either can't smell it at all or describe its smell as "musky".

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 29 30  0  0  0  0  0  0  0  0999 V2000
   -0.2467    1.3199    0.7613 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7971    0.6117   -0.1503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1016    0.5101   -1.3097 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1311    1.0707   -1.6461 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2313    0.6295   -0.7542 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7000    1.4046    0.2819 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7310    0.9756    1.1124 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3139   -0.2460    0.9171 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8654   -1.0432   -0.1121 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8328   -0.6045   -0.9378 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0861    0.0138    0.1747 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6461    0.2396    1.4421 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8435   -0.2675    1.8561 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5314   -1.0497    0.9555 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0631   -1.3228   -0.2999 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8204   -0.7749   -0.6793 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3776   -1.0625   -1.9345 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1016    2.1731   -1.7607 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3841    0.6861   -2.6784 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2621    2.3657    0.4540 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0715    1.6209    1.9211 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1229   -0.6367    1.5321 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2833   -2.0196   -0.3205 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4694   -1.2214   -1.7520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0888    0.8582    2.1368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2536   -0.0726    2.8529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4895   -1.4656    1.2631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6174   -1.9428   -1.0019 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5375   -0.7494   -2.3238 H   0  0  0  0  0  0  0  0  0  0  0  0
 17 16  1  0
 16 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 11  2  1  0
  2  1  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
 15 16  1  0
 10  5  1  0
 17 29  1  0
 12 25  1  0
 13 26  1  0
 14 27  1  0
 15 28  1  0
  4 18  1  0
  4 19  1  0
  6 20  1  0
  7 21  1  0
  8 22  1  0
  9 23  1  0
 10 24  1  0
M  END


  Mrv0541 02241214242D          

 17 18  0  0  0  0            999 V2000
   -0.7015   -1.2383    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7015   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0409    0.0004    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7015   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4447    0.0004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4447    0.8254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1879    1.2383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8486    0.8254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8486    0.0004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1879   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4447    0.0004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4447    0.8254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1054    1.2383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8486    0.8254    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8486    0.0004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1054   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7015    1.2383    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  2 11  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  5 10  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 11 12  2  0  0  0  0
 11 16  1  0  0  0  0
 12 13  1  0  0  0  0
 12 17  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0045464

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=C(C=CC=C1)C(=O)OCC1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C14H12O3/c15-13-9-5-4-8-12(13)14(16)17-10-11-6-2-1-3-7-11/h1-9,15H,10H2

> <INCHI_KEY>
ZCTQGTTXIYCGGC-UHFFFAOYSA-N

> <FORMULA>
C14H12O3

> <MOLECULAR_WEIGHT>
228.2433

> <EXACT_MASS>
228.07864425

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
23.66488658278388

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
benzyl 2-hydroxybenzoate

> <ALOGPS_LOGP>
3.66

> <JCHEM_LOGP>
4.047630575666666

> <ALOGPS_LOGS>
-3.31

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.715458839646441

> <JCHEM_PKA_STRONGEST_BASIC>
-4.287883324229868

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
64.67680000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.13e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
benzyl salicylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  O   UNK     0      -1.309  -2.311   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -1.309  -0.770   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       0.076   0.001   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       1.309  -0.770   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.697   0.001   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.697   1.541   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.084   2.311   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.317   1.541   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.317   0.001   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.084  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.697   0.001   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.697   1.541   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.930   2.311   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -5.317   1.541   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -5.317   0.001   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -3.930  -0.770   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -1.309   2.311   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   11                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   10                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    5    9                                                       
CONECT   11    2   12   16                                                  
CONECT   12   11   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   11   15                                                       
CONECT   17   12                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

View in JSmol

Synonyms

Value	Source
Benzyl salicylic acid	Generator
2-Hydroxybenzoic acid, phenylmethyl ester	HMDB
Benzoic acid, 2-hydroxy-, phenylmethyl ester	HMDB
Benzyl 2-hydroxybenzoate	HMDB
Benzyl O-hydroxybenzoate	HMDB
Benzyle salicylate	HMDB
FEMA 2151	HMDB
Phenylmethyl 2-hydroxybenzoate	HMDB
Salicyclic acid benzyl ester	HMDB
Salicyclic acid, benzyl ester	HMDB
Salicylic acid, benzyl ester	HMDB
Benzyl 2-hydroxybenzoic acid	Generator
Benzyl salicylate	MeSH

Chemical Formula

C₁₄H₁₂O₃

Average Mass

228.2433 Da

Monoisotopic Mass

228.07864 Da

IUPAC Name

benzyl 2-hydroxybenzoate

Traditional Name

benzyl salicylate

CAS Registry Number

118-58-1

SMILES

OC1=C(C=CC=C1)C(=O)OCC1=CC=CC=C1

InChI Identifier

InChI=1S/C14H12O3/c15-13-9-5-4-8-12(13)14(16)17-10-11-6-2-1-3-7-11/h1-9,15H,10H2

InChI Key

ZCTQGTTXIYCGGC-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, 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
Aniba affinis	LOTUS Database	35616633
Aniba terminalis	LOTUS Database	35616633
Antidesma laciniatum	LOTUS Database	35616633
Cananga odorata	Plant	KNApSAcK
Cedronella canariensis	LOTUS Database	35616633
Daphne papyracea	LOTUS Database	35616633
Desmos chinensis	LOTUS Database	35616633
Dianthus caryophyllus	Plant	KNApSAcK
Erica manipuliflora	LOTUS Database	35616633
Feijoa sellowiana	Plant	KNApSAcK
Lophomyrtus bullata	LOTUS Database	35616633
Murraya paniculata	Plant	KNApSAcK
Nicotiana cavicola	Plant	KNApSAcK
Plumeria obtusa	LOTUS Database	35616633
Plumeria rubra	LOTUS Database	35616633
Polygala senega	LOTUS Database	35616633
Populus	-	KNApSAcK
Primula spp.	Plant	KNApSAcK
Syzygium aromaticum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Uvaria grandiflora	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as o-hydroxybenzoic acid esters. These are benzoic acid esters where the benzene ring is ortho-substituted with a hydroxy group.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

o-Hydroxybenzoic acid esters

Alternative Parents

Substituents

O-hydroxybenzoic acid ester
Benzyloxycarbonyl
Salicylic acid or derivatives
Benzoyl
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Vinylogous acid
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organooxygen compound
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic 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	3.66	ALOGPS
logP	4.05	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	9.72	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	64.68 m³·mol⁻¹	ChemAxon
Polarizability	23.66 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon