NP-MRD: Showing NP-Card for Erythritol (NP0000691)

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Record Information

Version

2.0

Created at

2006-05-22 15:12:24 UTC

Updated at

2021-10-07 20:40:54 UTC

NP-MRD ID

NP0000691

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Erythritol

Description

Erythritol is a sugar alcohol (or polyol), used as a food additive and sugar substitute. It is naturally occurring and is made from corn using enzymes and fermentation. Its formula is C4H10O4, or HO(CH2)(CHOH)2(CH2)OH; specifically, one particular stereoisomer with that formula. Erythritol is 60–70% as sweet as sucrose (table sugar), yet it is almost noncaloric and does not affect blood sugar or cause tooth decay. Erythritol occurs widely in nature and has been found to occur naturally in several foods including wine, sake, beer, watermelon, pear, grape, and soy sauce. Evidence indicates that erythritol also exists endogenously in the tissues and body fluids of humans and animals. Erythritol is absorbed from the proximal intestine by passive diffusion in a manner similar to that of many low molecular weight organic molecules which do not have associated active transport systems. The rate of absorption is related to their molecular size. It passes through the intestinal membranes at a faster rate than larger molecules such as mannitol or glucose. In diabetics, erythritol has also been shown to be rapidly absorbed and excreted unchanged in the urine. Following absorption, ingested erythritol is rapidly distributed throughout the body and has been reported to occur in hepatocytes, pancreatic cells, and vascular smooth muscle cells. Erythritol also has been reported to cross the human placenta and to pass slowly from the plasma into the brain and cerebrospinal fluid (PMID: 9862657 ). Erythritol is found to be associated with ribose-5-phosphate isomerase deficiency, which is an inborn error of metabolism.

Structure

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


     RDKit          2D

 18 17  0  0  0  0  0  0  0  0999 V2000
   -2.8844   -1.1147    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6582   -0.2508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4320    0.6131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2959    1.8393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4320   -0.6131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2959   -1.8393    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6582    0.2508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8844    1.1147    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2457   -0.4847    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2401   -1.0317    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5221    0.9754    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2245    1.2077    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6659    3.2006    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2245   -1.2077    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6659   -3.2006    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2401    1.0317    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5221   -0.9754    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2457    0.4847    0.0000 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
  3  5  1  0
  5  6  1  0
  5  7  1  0
  7  8  1  0
  1  9  1  0
  2 10  1  6
  2 11  1  0
  3 12  1  1
  4 13  1  0
  5 14  1  6
  6 15  1  0
  7 16  1  6
  7 17  1  0
  8 18  1  0
M  END
> <DATABASE_ID>
NP0000691

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]OC([H])([H])[C@]([H])(O[H])[C@]([H])(O[H])C([H])([H])O[H]

> <INCHI_IDENTIFIER>
InChI=1S/C4H10O4/c5-1-3(7)4(8)2-6/h3-8H,1-2H2/t3-,4+

> <INCHI_KEY>
UNXHWFMMPAWVPI-ZXZARUISSA-N

> <FORMULA>
C4H10O4

> <MOLECULAR_WEIGHT>
122.1198

> <EXACT_MASS>
122.057908808

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
18

> <JCHEM_AVERAGE_POLARIZABILITY>
11.623273435855882

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3S)-butane-1,2,3,4-tetrol

> <ALOGPS_LOGP>
-2.03

> <JCHEM_LOGP>
-2.4693489646666666

> <ALOGPS_LOGS>
0.98

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.285181811808233

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.044993073077713

> <JCHEM_PKA_STRONGEST_BASIC>
-2.973906601202132

> <JCHEM_POLAR_SURFACE_AREA>
80.92

> <JCHEM_REFRACTIVITY>
26.478599999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.16e+03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
erythritol

> <JCHEM_VEBER_RULE>
0

$$$$

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  O   UNK     0       3.068  -0.019  -0.093  0.00  0.00           O+0
HETATM    2  C   UNK     0       1.853  -0.511  -0.588  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.758   0.133   0.217  0.00  0.00           C+0
HETATM    4  O   UNK     0       0.964  -0.235   1.562  0.00  0.00           O+0
HETATM    5  C   UNK     0      -0.616  -0.341  -0.198  0.00  0.00           C+0
HETATM    6  O   UNK     0      -0.876  -0.008  -1.509  0.00  0.00           O+0
HETATM    7  C   UNK     0      -1.615   0.424   0.677  0.00  0.00           C+0
HETATM    8  O   UNK     0      -2.906   0.064   0.337  0.00  0.00           O+0
HETATM    9  H   UNK     0       2.918   0.923   0.195  0.00  0.00           H+0
HETATM   10  H   UNK     0       1.721  -0.231  -1.665  0.00  0.00           H+0
HETATM   11  H   UNK     0       1.825  -1.613  -0.483  0.00  0.00           H+0
HETATM   12  H   UNK     0       0.815   1.216   0.094  0.00  0.00           H+0
HETATM   13  H   UNK     0       0.785  -1.216   1.591  0.00  0.00           H+0
HETATM   14  H   UNK     0      -0.731  -1.428  -0.079  0.00  0.00           H+0
HETATM   15  H   UNK     0      -1.755   0.420  -1.605  0.00  0.00           H+0
HETATM   16  H   UNK     0      -1.482   1.504   0.476  0.00  0.00           H+0
HETATM   17  H   UNK     0      -1.395   0.278   1.756  0.00  0.00           H+0
HETATM   18  H   UNK     0      -3.332   0.640  -0.323  0.00  0.00           H+0
CONECT    1    2    9                                                       
CONECT    2    1    3   10   11                                             
CONECT    3    2    4    5   12                                             
CONECT    4    3   13                                                       
CONECT    5    3    6    7   14                                             
CONECT    6    5   15                                                       
CONECT    7    5    8   16   17                                             
CONECT    8    7   18                                                       
CONECT    9    1                                                            
CONECT   10    2                                                            
CONECT   11    2                                                            
CONECT   12    3                                                            
CONECT   13    4                                                            
CONECT   14    5                                                            
CONECT   15    6                                                            
CONECT   16    7                                                            
CONECT   17    7                                                            
CONECT   18    8                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   34    0
END

View in JSmol

Synonyms

Value	Source
(2R,3S)-Butane-1,2,3,4-tetrol	ChEBI
Erythrit	ChEBI
Erythrite	ChEBI
Erythro-tetritol	ChEBI
Erythrol	ChEBI
L-Erythritol	ChEBI
MESO-erythritol	ChEBI
Mesoerythritol	ChEBI
Phycite	ChEBI
Phycitol	ChEBI
1,2,3,4-Butanetetrol	HMDB
Antierythrite	HMDB
Butanetetrol	HMDB
C*Eridex	HMDB
Erythroglucin	HMDB
I-erythritol	HMDB
L-(-)-Threitol	HMDB
L-Threitol	HMDB
Lichen sugar	HMDB
Meso-eythritol	HMDB
Paycite	HMDB
Tetrahydroxybutane	HMDB
1,2,3,4-Tetrahydroxybutane	HMDB

Chemical Formula

C₄H₁₀O₄

Average Mass

122.1198 Da

Monoisotopic Mass

122.05791 Da

IUPAC Name

(2R,3S)-butane-1,2,3,4-tetrol

Traditional Name

erythritol

CAS Registry Number

149-32-6

SMILES

[H]OC([H])([H])[C@]([H])(O[H])[C@]([H])(O[H])C([H])([H])O[H]

InChI Identifier

InChI=1S/C4H10O4/c5-1-3(7)4(8)2-6/h3-8H,1-2H2/t3-,4+

InChI Key

UNXHWFMMPAWVPI-ZXZARUISSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

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
Allium chinense	LOTUS Database	35616633
Anas platyrhynchos	FooDB	FooDB
Anatidae	FooDB	FooDB
Anethum graveolens	LOTUS Database	35616633
Annona squamosa	LOTUS Database	35616633
Anser anser	FooDB	FooDB
Arabidopsis thaliana	KNApSAcK Database	22123792
Aspergillus ochraceus	LOTUS Database	35616633
Bergera koenegii	-	KNApSAcK
Bison bison	FooDB	FooDB
Bos taurus	FooDB	FooDB
Bos taurus X Bison bison	FooDB	FooDB
Bubalus bubalis	FooDB	FooDB
Cajanus cajan	LOTUS Database	35616633
Cannabis sativa	CannabisDB	Not Available
Capra aegagrus hircus	FooDB	FooDB
Carum carvi	FooDB	KNAPSACK
Carum carvi L.	KNApSAcK Database	22123792
Cervidae	FooDB	FooDB
Cervus canadensis	FooDB	FooDB
Citrus sinensis	KNApSAcK Database	22123792
Citrus X sinensis (L.) Osbeck (pro. sp.)	Plant	KNApSAcK
Cnidium monnieri	LOTUS Database	35616633
Columba	FooDB	FooDB
Columbidae	FooDB	FooDB
Curcuma domestica	KNApSAcK Database	22123792
Curcuma longa	Plant	KNApSAcK
Delonix regia	KNApSAcK Database	22123792
Dromaius novaehollandiae	FooDB	FooDB
Equus caballus	FooDB	FooDB
Euphorbia plumerioides	LOTUS Database	35616633
Foeniculum vulgare	LOTUS Database	35616633
Gallus gallus	FooDB	FooDB
Glehnia littoralis	LOTUS Database	35616633
Lagopus muta	FooDB	FooDB
Leporidae	FooDB	FooDB
Lepus timidus	FooDB	FooDB
Lotus corniculatus	LOTUS Database	35616633
Melanitta fusca	FooDB	FooDB
Meleagris gallopavo	FooDB	FooDB
Murraya paniculata	KNApSAcK Database	22123792
Numida meleagris	FooDB	FooDB
Odocoileus	FooDB	FooDB
Oryctolagus	FooDB	FooDB
Ovis aries	FooDB	FooDB
Phasianidae	FooDB	FooDB
Phasianus colchicus	FooDB	FooDB
Primula spp.	KNApSAcK Database	22123792
Ramalina usnea	LOTUS Database	35616633
Roccellaria mollis	LOTUS Database	35616633
Salacia chinensis	LOTUS Database	35616633
Solanum lycopersicum	FooDB	KNAPSACK
Solanum lycopersicum L.	KNApSAcK Database	22123792
Struthio camelus	FooDB	FooDB
Sus scrofa	FooDB	FooDB
Sus scrofa domestica	FooDB	FooDB

Species Where Detected

Species Name	Source	Reference
Homo sapiens (Urine)	KNApSAcK Database	22123792

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sugar alcohols. These are hydrogenated forms of carbohydrate in which the carbonyl group (aldehyde or ketone, reducing sugar) has been reduced to a primary or secondary hydroxyl group.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Sugar alcohols

Alternative Parents

Substituents

Sugar alcohol
Secondary alcohol
Polyol
Hydrocarbon derivative
Primary alcohol
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

butane-1,2,3,4-tetrol (CHEBI:17113 )

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	121.5 °C	Not Available
Boiling Point	330.00 to 331.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	610 mg/mL at 22 °C	Not Available
LogP	-2.29	Hansch CH, Leo A and Hoekman DH. "Exploring QSAR: Hydrophobic, Electronic, and Steric Constraints. Volume 1" ACS Publications (1995).

Predicted Properties

Property	Value	Source
Water Solubility	1160 g/L	ALOGPS
logP	-2	ALOGPS
logP	-2.5	ChemAxon
logS	0.98	ALOGPS
pKa (Strongest Acidic)	13.04	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	80.92 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	26.48 m³·mol⁻¹	ChemAxon
Polarizability	11.62 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

HMDB0002994

DrugBank ID

DB04481

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

ChEBI ID

Good Scents ID

References

General References

Verhoeven NM, Huck JH, Roos B, Struys EA, Salomons GS, Douwes AC, van der Knaap MS, Jakobs C: Transaldolase deficiency: liver cirrhosis associated with a new inborn error in the pentose phosphate pathway. Am J Hum Genet. 2001 May;68(5):1086-92. Epub 2001 Mar 27. [PubMed:11283793 ]
Prandi D: Canalicular bile production in man. Eur J Clin Invest. 1975 Feb;5(1):1-6. [PubMed:1122919 ]
Makinen KK, Isotupa KP, Kivilompolo T, Makinen PL, Toivanen J, Soderling E: Comparison of erythritol and xylitol saliva stimulants in the control of dental plaque and mutans streptococci. Caries Res. 2001 Mar-Apr;35(2):129-35. [PubMed:11275673 ]
Hino H, Kobayasi T, Asboe-Hansen G: Desmosome formation in normal human epidermal cell culture. Acta Derm Venereol. 1982;62(3):185-91. [PubMed:6179356 ]
Bornet FR, Blayo A, Dauchy F, Slama G: Gastrointestinal response and plasma and urine determinations in human subjects given erythritol. Regul Toxicol Pharmacol. 1996 Oct;24(2 Pt 2):S296-302. [PubMed:8933646 ]
Noda K, Nakayama K, Oku T: Serum glucose and insulin levels and erythritol balance after oral administration of erythritol in healthy subjects. Eur J Clin Nutr. 1994 Apr;48(4):286-92. [PubMed:8039489 ]
Makinen KK, Saag M, Isotupa KP, Olak J, Nommela R, Soderling E, Makinen PL: Similarity of the effects of erythritol and xylitol on some risk factors of dental caries. Caries Res. 2005 May-Jun;39(3):207-15. [PubMed:15914983 ]
Servo C, Palo J, Pitkanen E: Gas chromatographic separation and mass spectrometric identification of polyols in human cerebrospinal fluid and plasma. Acta Neurol Scand. 1977 Aug;56(2):104-10. [PubMed:899714 ]
Utili R, Abernathy CO, Zimmerman HJ: Studies on the effects of C. coli endotoxin on canalicular bile formation in the isolated perfused rat liver. J Lab Clin Med. 1977 Mar;89(3):471-82. [PubMed:320281 ]
Munro IC, Berndt WO, Borzelleca JF, Flamm G, Lynch BS, Kennepohl E, Bar EA, Modderman J: Erythritol: an interpretive summary of biochemical, metabolic, toxicological and clinical data. Food Chem Toxicol. 1998 Dec;36(12):1139-74. [PubMed:9862657 ]

Showing NP-Card for Erythritol (NP0000691)

MOL for NP0000691 (Erythritol)

3D MOL for NP0000691 (Erythritol)

3D SDF for NP0000691 (Erythritol)

3D-SDF for NP0000691 (Erythritol)

PDB for NP0000691 (Erythritol)

3D PDB for NP0000691 (Erythritol)

SMILES for NP0000691 (Erythritol)

INCHI for NP0000691 (Erythritol)

Structure for NP0000691 (Erythritol)

3D Structure for NP0000691 (Erythritol)