NP-MRD: Showing NP-Card for Triacetin (NP0045422)

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Record Information

Version

1.0

Created at

2022-03-17 19:19:42 UTC

Updated at

2022-03-17 19:19:42 UTC

NP-MRD ID

NP0045422

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Triacetin

Description

Triacetin, also known as enzactin or fungacet, belongs to the class of organic compounds known as triacylglycerols. These are glycerides consisting of three fatty acid chains covalently bonded to a glycerol molecule through ester linkages. Thus, triacetin is considered to be a triradylglycerol lipid molecule. Triacetin is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Triacetin is a mild, bitter, and clean tasting compound. Outside of the human body, Triacetin has been detected, but not quantified in, fruits and papaya. This could make triacetin a potential biomarker for the consumption of these foods. Triacetin is found in Carica papay and Vitis vinifera. It was first documented in 1959 (PMID: 14404545). A triglyceride obtained by acetylation of the three hydroxy groups of glycerol (PMID: 14555416) (PMID: 23293041) (PMID: 23996800) (PMID: 24574778) (PMID: 23340101) (PMID: 22396747).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 29 28  0  0  0  0  0  0  0  0999 V2000
    3.2179   -2.2379   -0.3655 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4272   -1.1255    0.2843 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8528    0.0535    0.2739 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2215   -1.3680    0.9051 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3885   -0.4663    1.5339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1876    0.6340    0.7285 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1146    0.1502   -0.3679 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0468   -0.7336    0.2059 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0219   -1.3291   -0.5826 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0341   -2.2759   -0.0131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0260   -1.0436   -1.8019 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7320    1.5140    0.1277 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7171    2.8521    0.4185 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6447    3.8536   -0.1638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1451    3.2750    1.2411 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8678   -2.4404   -1.3841 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2691   -1.8860   -0.3843 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1908   -3.1474    0.2641 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8327   -0.0323    2.4767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4947   -1.0511    1.9354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8550    1.2303    1.4211 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5524   -0.2956   -1.2083 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6492    1.0623   -0.7449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1094   -3.1341   -0.7265 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7262   -2.6694    0.9555 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0328   -1.8306    0.0414 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1411    4.5062   -0.9110 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9616    4.5260    0.6596 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5308    3.4096   -0.6219 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  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  1  0
  9 11  2  0
  6 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  2  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  5 19  1  0
  5 20  1  0
  6 21  1  0
  7 22  1  0
  7 23  1  0
 10 24  1  0
 10 25  1  0
 10 26  1  0
 14 27  1  0
 14 28  1  0
 14 29  1  0
M  END


  Mrv0541 05061304492D          

 15 14  0  0  0  0            999 V2000
    5.8263   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1105   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6829   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6829    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1118    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6829   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9684   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1118    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3974   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3974   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.9684   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  1  0  0  0  0
  7  2  1  0  0  0  0
  8  3  1  0  0  0  0
  9  4  1  0  0  0  0
  9  5  1  0  0  0  0
 10  6  2  0  0  0  0
 11  7  2  0  0  0  0
 12  8  2  0  0  0  0
 13  4  1  0  0  0  0
 13  6  1  0  0  0  0
 14  5  1  0  0  0  0
 14  7  1  0  0  0  0
 15  8  1  0  0  0  0
 15  9  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0045422

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OCC(COC(C)=O)OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C9H14O6/c1-6(10)13-4-9(15-8(3)12)5-14-7(2)11/h9H,4-5H2,1-3H3

> <INCHI_KEY>
URAYPUMNDPQOKB-UHFFFAOYSA-N

> <FORMULA>
C9H14O6

> <MOLECULAR_WEIGHT>
218.2039

> <EXACT_MASS>
218.07903818

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
20.883193605477576

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
1,3-bis(acetyloxy)propan-2-yl acetate

> <ALOGPS_LOGP>
0.40

> <JCHEM_LOGP>
-0.5156377916666666

> <ALOGPS_LOGS>
-1.29

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.526940023025307

> <JCHEM_POLAR_SURFACE_AREA>
78.9

> <JCHEM_REFRACTIVITY>
47.97060000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.13e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
triacetin

> <JCHEM_VEBER_RULE>
0

$$$$

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      10.876  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.206  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.875  -4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.875   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.207   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       9.542   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.875  -3.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.541  -0.770   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       9.542   1.540   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0       1.540   1.540   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       8.208  -2.310   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       8.208  -0.770   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       2.874  -0.770   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       5.541  -2.310   0.000  0.00  0.00           O+0
CONECT    1    6                                                            
CONECT    2    7                                                            
CONECT    3    8                                                            
CONECT    4    9   13                                                       
CONECT    5    9   14                                                       
CONECT    6    1   10   13                                                  
CONECT    7    2   11   14                                                  
CONECT    8    3   12   15                                                  
CONECT    9    4    5   15                                                  
CONECT   10    6                                                            
CONECT   11    7                                                            
CONECT   12    8                                                            
CONECT   13    4    6                                                       
CONECT   14    5    7                                                       
CONECT   15    8    9                                                       
MASTER        0    0    0    0    0    0    0    0   15    0   28    0
END

View in JSmol

Synonyms

Value	Source
1,2,3-Propanetriol triacetate	ChEBI
1,2,3-Propanetriyl triacetate	ChEBI
1,2,3-Triacetoxypropane	ChEBI
1,2,3-Triacetylglycerol	ChEBI
2-(Acetyloxy)-1-[(acetyloxy)methyl]ethyl acetate	ChEBI
e 1518	ChEBI
e-1518	ChEBI
e1518	ChEBI
Enzactin	ChEBI
Glycerin triacetate	ChEBI
Glycerol triacetate	ChEBI
Glyceryl triacetate	ChEBI
Triacetina	ChEBI
Triacetine	ChEBI
Triacetinum	ChEBI
Triacetyl glycerin	ChEBI
Triacetyl glycerine	ChEBI
Triacetylglycerol	ChEBI
1,2,3-Propanetriol triacetic acid	Generator
1,2,3-Propanetriyl triacetic acid	Generator
2-(Acetyloxy)-1-[(acetyloxy)methyl]ethyl acetic acid	Generator
Glycerin triacetic acid	Generator
Glycerol triacetic acid	Generator
Glyceryl triacetic acid	Generator
1,2,3-Propanetriol triacetate, 9ci	HMDB
1,2,3-Propanetriol, 1,2,3-triacetate	HMDB
1,2,3-Propanetriol, triacetate	HMDB
Acetic, 1,2,3-propanetriyl ester	HMDB
Blekin	HMDB
Enzacetin	HMDB
Estol 1581	HMDB
Euzactin	HMDB
FEMA 2007	HMDB
Fungacet	HMDB
Fungacetin	HMDB
Glycerol triacetate tributyrin	HMDB
Glyped	HMDB
Kesscoflex tra	HMDB
Kodaflex triacetin	HMDB
Motisil	HMDB
Propane-1,2,3-triyl triacetate	HMDB
Tri-acetin	HMDB
Triacetin (1,2,3-propanetriol triacetate)	HMDB
Triacetin (glycerol triacetate)	HMDB
Triacetin, 8ci, ban, inn, usan	HMDB
Triacetyl glycerol	HMDB
Vanay	HMDB
Triacetyl-glycerol	HMDB

Chemical Formula

C₉H₁₄O₆

Average Mass

218.2039 Da

Monoisotopic Mass

218.07904 Da

IUPAC Name

1,3-bis(acetyloxy)propan-2-yl acetate

Traditional Name

triacetin

CAS Registry Number

102-76-1

SMILES

CC(=O)OCC(COC(C)=O)OC(C)=O

InChI Identifier

InChI=1S/C9H14O6/c1-6(10)13-4-9(15-8(3)12)5-14-7(2)11/h9H,4-5H2,1-3H3

InChI Key

URAYPUMNDPQOKB-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
Carica papay	Plant	KNApSAcK
Carica papaya L.	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Vitis vinifera	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as triacylglycerols. These are glycerides consisting of three fatty acid chains covalently bonded to a glycerol molecule through ester linkages.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Glycerolipids

Sub Class

Triradylcglycerols

Direct Parent

Triacylglycerols

Alternative Parents

Substituents

Triacyl-sn-glycerol
Tricarboxylic acid or derivatives
Carboxylic acid ester
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

triglyceride (CHEBI:9661 )
Triacylglycerols (LMGL03012615 )

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	0.4	ALOGPS
logP	-0.52	ChemAxon
logS	-1.3	ALOGPS
pKa (Strongest Basic)	-6.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	78.9 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	47.97 m³·mol⁻¹	ChemAxon
Polarizability	20.88 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0029592

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB000751

KNApSAcK ID

Not Available

Chemspider ID

13835706

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Triacetin

METLIN ID

Not Available

PubChem Compound

5541

PDB ID

Not Available

ChEBI ID

9661

Good Scents ID

Not Available

References

General References

Fiume MZ: Final report on the safety assessment of triacetin. Int J Toxicol. 2003;22 Suppl 2:1-10. [PubMed:14555416 ]
Choudhury H, Gorain B, Karmakar S, Pal TK: Development and validation of RP-HPLC method: scope of application in the determination of oil solubility of paclitaxel. J Chromatogr Sci. 2014 Jan;52(1):68-74. doi: 10.1093/chromsci/bms206. Epub 2013 Jan 4. [PubMed:23293041 ]
Tsen AR, Long PM, Driscoll HE, Davies MT, Teasdale BA, Penar PL, Pendlebury WW, Spees JL, Lawler SE, Viapiano MS, Jaworski DM: Triacetin-based acetate supplementation as a chemotherapeutic adjuvant therapy in glioma. Int J Cancer. 2014 Mar 15;134(6):1300-10. doi: 10.1002/ijc.28465. Epub 2013 Sep 30. [PubMed:23996800 ]
Oosaka K, Tokuda M, Furukawa N: Intra-gastric triacetin alters upper gastrointestinal motility in conscious dogs. World J Gastroenterol. 2014 Jan 28;20(4):1054-60. doi: 10.3748/wjg.v20.i4.1054. [PubMed:24574778 ]
Goembira F, Saka S: Optimization of biodiesel production by supercritical methyl acetate. Bioresour Technol. 2013 Mar;131:47-52. doi: 10.1016/j.biortech.2012.12.130. Epub 2012 Dec 27. [PubMed:23340101 ]
Brault G, Shareck F, Hurtubise Y, Lepine F, Doucet N: Isolation and characterization of EstC, a new cold-active esterase from Streptomyces coelicolor A3(2). PLoS One. 2012;7(3):e32041. doi: 10.1371/journal.pone.0032041. Epub 2012 Mar 2. [PubMed:22396747 ]
KARNS ME, PARKER R: The treatment of refractory fungus infections with fungacetin (triacetin). J Am Podiatry Assoc. 1959 Sep;49:411-2. [PubMed:14404545 ]
Cheng M, Angkawidjaja C, Koga Y, Kanaya S: Requirement of lid2 for interfacial activation of a family I.3 lipase with unique two lid structures. FEBS J. 2012 Oct;279(19):3727-3737. doi: 10.1111/j.1742-4658.2012.08734.x. Epub 2012 Aug 31. [PubMed:22863357 ]
Malik B, Benaissa M: Determination of glucose concentration from near-infrared spectra using locally weighted partial least square regression. Annu Int Conf IEEE Eng Med Biol Soc. 2012;2012:6169-71. doi: 10.1109/EMBC.2012.6347402. [PubMed:23367337 ]
Sarkar B, Ravi V, Alexandridis P: Micellization of amphiphilic block copolymers in binary and ternary solvent mixtures. J Colloid Interface Sci. 2013 Jan 15;390(1):137-46. doi: 10.1016/j.jcis.2012.09.028. Epub 2012 Sep 26. [PubMed:23099248 ]

Showing NP-Card for Triacetin (NP0045422)

MOL for NP0045422 (Triacetin)

3D MOL for NP0045422 (Triacetin)

3D SDF for NP0045422 (Triacetin)

3D-SDF for NP0045422 (Triacetin)

PDB for NP0045422 (Triacetin)

3D PDB for NP0045422 (Triacetin)

SMILES for NP0045422 (Triacetin)

INCHI for NP0045422 (Triacetin)

Structure for NP0045422 (Triacetin)

3D Structure for NP0045422 (Triacetin)