NP-MRD: Showing NP-Card for phenol, o-octyl- (NP0160362)

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Record Information

Version

2.0

Created at

2022-09-02 18:18:25 UTC

Updated at

2022-09-02 18:18:25 UTC

NP-MRD ID

NP0160362

Secondary Accession Numbers

None

Natural Product Identification

Common Name

phenol, o-octyl-

Description

Octylphenol belongs to the class of organic compounds known as 1-hydroxy-4-unsubstituted benzenoids. These are phenols that are unsubstituted at the 4-position. Uses of long-chain alkylphenols The long-chain alkylphenols are used extensively as precursors to the detergents, as additives for fuels and lubricants, polymers, and as components in phenolic resins. These compounds are also used as building block chemicals that are also used in making fragrances, thermoplastic elastomers, antioxidants, oil field chemicals and fire retardant materials. Octylphenol is an extremely weak basic (essentially neutral) compound (based on its pKa). Alkylphenols are a family of organic compounds obtained by the alkylation of phenols. The long-chain alkylphenols are prepared by alkylation of phenol with alkenes:C6H5OH + RR'CCHR" → RR'CH−CHR"−C6H4OHIn this way, about 500M kg/y are produced. Through the downstream use in making alkylphenolic resins, alkylphenols are also found in tires, adhesives, coatings, carbonless copy paper and high performance rubber products. The European Union has implemented sales and use restrictions on certain applications in which nonylphenols are used because of their alleged "toxicity, persistence, and the liability to bioaccumulate" but the United States EPA has taken a slower approach to make sure that action is based on sound science. Methylphenols and ethylphenols are also alkylphenols, but they are more commonly referred to by their specific names, cresols and xylenols. phenol, o-octyl- is found in Ligusticum chuanxiong. They have been used in industry for over 40 years.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 37 37  0  0  0  0  0  0  0  0999 V2000
    5.2145    0.9984    1.2226 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1057   -0.0167    1.5405 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1177    0.0781    0.4316 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9407   -0.8473    0.5562 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0647   -0.5996   -0.6551 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1532   -1.4988   -0.6077 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0481   -1.2648   -1.7656 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7023    0.0572   -1.8961 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6690    0.4245   -0.8596 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0228    0.2111   -1.1690 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0316    0.4787   -0.3045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7631    0.9842    0.9454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4565    1.2073    1.2864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4312    0.9250    0.3803 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1529    1.1700    0.7734 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4527    0.8545    0.1562 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0546    0.9276    1.9077 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6951    1.9995    1.2730 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5904   -1.0120    1.6117 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7291    0.2554    2.5293 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7708    1.1197    0.3462 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6404   -0.1865   -0.5144 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2755   -1.9051    0.5416 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3823   -0.7046    1.5031 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8386    0.4429   -0.8186 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6577   -0.9851   -1.5519 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2377   -2.5461   -0.7045 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6963   -1.4671    0.3374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5594   -1.5309   -2.7377 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8750   -2.0412   -1.6836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2310    0.0713   -2.8917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9106    0.8491   -2.0293 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2756   -0.1874   -2.1470 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0848    0.3008   -0.5728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5815    1.1958    1.6286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1905    1.6032    2.2573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9329    1.5395    1.6807 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  2  0
 14 15  1  0
 14  9  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  2 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  5 25  1  0
  5 26  1  0
  6 27  1  0
  6 28  1  0
  7 29  1  0
  7 30  1  0
  8 31  1  0
  8 32  1  0
 10 33  1  0
 11 34  1  0
 12 35  1  0
 13 36  1  0
 15 37  1  0
M  END


  Mrv1572004191603522D          

 15 15  0  0  0  0            999 V2000
    2.1434    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  3  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  1  0  0  0  0
  9  8  2  0  0  0  0
 10  7  1  0  0  0  0
 11  8  1  0  0  0  0
 12  9  1  0  0  0  0
 13 10  1  0  0  0  0
 13 11  2  0  0  0  0
 14 12  2  0  0  0  0
 14 13  1  0  0  0  0
 15 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0160362

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCCC1=CC=CC=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C14H22O/c1-2-3-4-5-6-7-10-13-11-8-9-12-14(13)15/h8-9,11-12,15H,2-7,10H2,1H3

> <INCHI_KEY>
DUIOKRXOKLLURE-UHFFFAOYSA-N

> <FORMULA>
C14H22O

> <MOLECULAR_WEIGHT>
206.329

> <EXACT_MASS>
206.167065328

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
26.204277559684073

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-octylphenol

> <ALOGPS_LOGP>
5.38

> <JCHEM_LOGP>
5.295082538666668

> <ALOGPS_LOGS>
-4.61

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.296631858080396

> <JCHEM_PKA_STRONGEST_BASIC>
-5.472857436974995

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
65.28710000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.05e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
phenol, o-octyl-

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 19-APR-16   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-16         0                                  
HETATM    1  C   UNK     0       4.001  11.550   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.335  10.780   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.668  11.550   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.002  10.780   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.336  11.550   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      10.669  10.780   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      12.003  11.550   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      17.338  11.550   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      17.338  13.090   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      13.337  10.780   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      16.004  10.780   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      16.004  13.860   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      14.670  11.550   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      14.670  13.090   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      13.337  13.860   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6   10                                                       
CONECT    8    9   11                                                       
CONECT    9    8   12                                                       
CONECT   10    7   13                                                       
CONECT   11    8   13                                                       
CONECT   12    9   14                                                       
CONECT   13   10   11   14                                                  
CONECT   14   12   13   15                                                  
CONECT   15   14                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

View in JSmol

Synonyms

Value	Source
Octylphenol	MeSH

Chemical Formula

C₁₄H₂₂O

Average Mass

206.3290 Da

Monoisotopic Mass

206.16707 Da

IUPAC Name

2-octylphenol

Traditional Name

phenol, o-octyl-

CAS Registry Number

Not Available

SMILES

CCCCCCCCC1=CC=CC=C1O

InChI Identifier

InChI=1S/C14H22O/c1-2-3-4-5-6-7-10-13-11-8-9-12-14(13)15/h8-9,11-12,15H,2-7,10H2,1H3

InChI Key

DUIOKRXOKLLURE-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
Ligusticum chuanxiong	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 1-hydroxy-4-unsubstituted benzenoids. These are phenols that are unsubstituted at the 4-position.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Phenols

Sub Class

1-hydroxy-4-unsubstituted benzenoids

Direct Parent

1-hydroxy-4-unsubstituted benzenoids

Alternative Parents

Substituents

1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
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	5.38	ALOGPS
logP	5.3	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	10.3	ChemAxon
pKa (Strongest Basic)	-5.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	65.29 m³·mol⁻¹	ChemAxon
Polarizability	26.2 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Alkylphenol

METLIN ID

Not Available

PubChem Compound

13700

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for phenol, o-octyl- (NP0160362)

MOL for NP0160362 (phenol, o-octyl-)

3D MOL for NP0160362 (phenol, o-octyl-)

3D SDF for NP0160362 (phenol, o-octyl-)

3D-SDF for NP0160362 (phenol, o-octyl-)

PDB for NP0160362 (phenol, o-octyl-)

3D PDB for NP0160362 (phenol, o-octyl-)

SMILES for NP0160362 (phenol, o-octyl-)

INCHI for NP0160362 (phenol, o-octyl-)

Structure for NP0160362 (phenol, o-octyl-)

3D Structure for NP0160362 (phenol, o-octyl-)