NP-MRD: Showing NP-Card for (±)-Benzoin (NP0336832)

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Record Information

Version

2.0

Created at

2024-09-11 08:02:01 UTC

Updated at

2024-09-11 08:02:02 UTC

NP-MRD ID

NP0336832

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(±)-Benzoin

Description

Benzoin is also known as PHCH(OH)COPH. (±)-Benzoin was first documented in 2024 (PMID: 39239291). Based on a literature review a significant number of articles have been published on benzoin (PMID: 39163701) (PMID: 39133951) (PMID: 39108164) (PMID: 39052990) (PMID: 38877788) (PMID: 38864298).

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 05262310342D          

 16 17  0  0  0  0            999 V2000
   -4.6554   -3.9777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3698   -4.3902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3698   -5.2152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6554   -5.6277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9409   -5.2152    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9409   -4.3902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2264   -3.9777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5119   -4.3902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7975   -3.9777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0830   -2.7402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7975   -3.1527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0830   -4.3902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3685   -3.9777    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3685   -3.1527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2264   -3.1527    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5120   -5.2152    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
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
 11  9  2  0  0  0  0
  9 12  1  0  0  0  0
 10 11  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 10 14  2  0  0  0  0
  7 15  1  0  0  0  0
  8 16  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0336832

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC(C(=O)C1=CC=CC=C1)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1/C14H12O2/c15-13(11-7-3-1-4-8-11)14(16)12-9-5-2-6-10-12/h1-10,13,15H

> <INCHI_KEY>
ISAOCJYIOMOJEB-UHFFFAOYNA-N

> <FORMULA>
C14H12O2

> <MOLECULAR_WEIGHT>
212.248

> <EXACT_MASS>
212.083729626

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
28

> <JCHEM_AVERAGE_POLARIZABILITY>
22.50247166089089

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-hydroxy-1,2-diphenylethan-1-one

> <JCHEM_LOGP>
2.650074693666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.617339760665859

> <JCHEM_PKA_STRONGEST_BASIC>
-3.8407029979448226

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
62.52090000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(+-)-benzoin

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 26-MAY-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-23         0                                  
HETATM    1  C   UNK     0      -8.690  -7.425   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -10.024  -8.195   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -10.024  -9.735   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -8.690 -10.505   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -7.356  -9.735   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -7.356  -8.195   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -6.023  -7.425   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.689  -8.195   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.355  -7.425   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.022  -5.115   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.355  -5.885   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.022  -8.195   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.688  -7.425   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.688  -5.885   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -6.023  -5.885   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      -4.689  -9.735   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    1    7                                                  
CONECT    7    6    8   15                                                  
CONECT    8    7    9   16                                                  
CONECT    9    8   11   12                                                  
CONECT   10   11   14                                                       
CONECT   11    9   10                                                       
CONECT   12    9   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   10                                                       
CONECT   15    7                                                            
CONECT   16    8                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

View in JSmol

Synonyms

Value	Source
2-Hydroxy-1,2-diphenylethanone	ChEBI
2-Hydroxy-2-phenylacetophenone	ChEBI
alpha-Hydroxy-alpha-phenylacetophenone	ChEBI
alpha-Hydroxybenzyl phenyl ketone	ChEBI
Benzoylphenylcarbinol	ChEBI
Hydroxy-2-phenyl acetophenone	ChEBI
PHCH(OH)COPH	ChEBI
PHCOCH(OH)PH	ChEBI
Phenyl-alpha-hydroxybenzyl ketone	ChEBI
Phenylbenzoyl carbinol	ChEBI
a-Hydroxy-a-phenylacetophenone	Generator
Α-hydroxy-α-phenylacetophenone	Generator
a-Hydroxybenzyl phenyl ketone	Generator
Α-hydroxybenzyl phenyl ketone	Generator
Phenyl-a-hydroxybenzyl ketone	Generator
Phenyl-α-hydroxybenzyl ketone	Generator

Chemical Formula

C₁₄H₁₂O₂

Average Mass

212.2480 Da

Monoisotopic Mass

212.08373 Da

IUPAC Name

2-hydroxy-1,2-diphenylethan-1-one

Traditional Name

(+-)-benzoin

CAS Registry Number

Not Available

SMILES

OC(C(=O)C1=CC=CC=C1)C1=CC=CC=C1

InChI Identifier

InChI=1/C14H12O2/c15-13(11-7-3-1-4-8-11)14(16)12-9-5-2-6-10-12/h1-10,13,15H

InChI Key

ISAOCJYIOMOJEB-UHFFFAOYNA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Classification

Not classified

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	2.65	ChemAxon
pKa (Strongest Acidic)	12.62	ChemAxon
pKa (Strongest Basic)	-3.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	62.52 m³·mol⁻¹	ChemAxon
Polarizability	22.5 Å³	ChemAxon
Number of Rings	2	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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00059369

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Benzoin

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

17682

Good Scents ID

Not Available

References

General References

Kadu VD, Thokal MS, Godase RK, Kotali BC, Wadkar PS: Metal-free approach for imidazole synthesis via one-pot N-alpha-C(sp(3))-H bond functionalization of benzylamines. RSC Adv. 2024 Sep 5;14(39):28332-28339. doi: 10.1039/d4ra03939d. eCollection 2024 Sep 4. [PubMed:39239291 ]
Wu Y, Li Y, Li S, Ma Y, Ji W, Sun Y: The series of L-lysine-derived gelators-modified multifunctional chromatography stationary phase for separation of chiral and achiral compounds. J Chromatogr A. 2024 Sep 27;1733:465228. doi: 10.1016/j.chroma.2024.465228. Epub 2024 Aug 7. [PubMed:39163701 ]
Yu LQ, Liang RX, Chen J, Xie SM, Wang BJ, Zhang JH, Yuan LM: Preparation and evaluation of a 1,1'-bi-2-naphthol-based chiral macrocycle bonded silica chiral stationary phase for high performance liquid chromatography. J Chromatogr A. 2024 Sep 13;1732:465231. doi: 10.1016/j.chroma.2024.465231. Epub 2024 Aug 9. [PubMed:39133951 ]
Zhang Y, Lu YR, Liu C, Ma AX, Luo ZH, Zhou HM, Zhang JH, Wang BJ, Xie SM, Yuan LM: Room temperature synthesis of a chiral covalent organic framework core-shell composite for high-performance liquid chromatography enantioseparation. J Sep Sci. 2024 Aug;47(15):e2400140. doi: 10.1002/jssc.202400140. [PubMed:39108164 ]
Abou-Ezze K, Llevot A, Taton D: Exploiting the Reversible Dimerization of N-Heterocyclic Carbenes to Access Dynamic Polymer Networks with an Organocatalytic Activity. ACS Macro Lett. 2024 Aug 20;13(8):1008-1015. doi: 10.1021/acsmacrolett.4c00390. Epub 2024 Jul 25. [PubMed:39052990 ]
Wang Y, Huang Z, Zhou T, Li C, Sun Y, Pang J: Progress of research on aroma absorption mechanism and aroma fixation pathway of jasmine green tea. J Sci Food Agric. 2024 Jun 15. doi: 10.1002/jsfa.13656. [PubMed:38877788 ]
Li C, Cheng J, Wan X, Li J, Zu W, Xu Y, Huang Y, Huo H: Ni/Photoredox-Catalyzed Enantioselective Acylation of alpha-Bromobenzoates with Aldehydes: A Formal Approach to Aldehyde-Aldehyde Cross-Coupling. J Am Chem Soc. 2024 Jul 24;146(29):19909-19918. doi: 10.1021/jacs.4c03164. Epub 2024 Jun 12. [PubMed:38864298 ]
Aysin RR, Galkin KI: Impact of Backbone Substitution on Organocatalytic Activity of Sterically Encumbered NHC in Benzoin Condensation. Molecules. 2024 Apr 10;29(8):1704. doi: 10.3390/molecules29081704. [PubMed:38675524 ]
Baranska I, Osmialowski B, Rafinska K, Rafinski Z: Construction of Highly Functionalized 2-Styrylfurans by N-Heterocyclic Carbene/Bronsted Acid Catalysis. Org Lett. 2024 May 3;26(17):3514-3518. doi: 10.1021/acs.orglett.4c00836. Epub 2024 Apr 23. [PubMed:38651753 ]

Showing NP-Card for (±)-Benzoin (NP0336832)

MOL for NP0336832 ((±)-Benzoin)

3D MOL for NP0336832 ((±)-Benzoin)

3D SDF for NP0336832 ((±)-Benzoin)

3D-SDF for NP0336832 ((±)-Benzoin)

PDB for NP0336832 ((±)-Benzoin)

3D PDB for NP0336832 ((±)-Benzoin)

SMILES for NP0336832 ((±)-Benzoin)

INCHI for NP0336832 ((±)-Benzoin)

Structure for NP0336832 ((±)-Benzoin)

3D Structure for NP0336832 ((±)-Benzoin)