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Details

Stereochemistry ACHIRAL
Molecular Formula C4H10O4
Molecular Weight 122.1198
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ERYTHRITOL

SMILES

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

InChI

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

HIDE SMILES / InChI

Molecular Formula C4H10O4
Molecular Weight 122.1198
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Erythritol is a four carbon sugar that is found in algae, fungi, and lichens. It is twice as sweet as sucrose and has been approved by the United States and EU Food and Drug Administrations for use as a low-calorie sweetener. Erythritol is well tolerated and elicits no toxicological effects. It is rapidly absorbed and quantitatively excreted without metabolic change. Erythritol has been investigated as a food supplement to treat Endothelial Function related to Type II diabetes. It has also been studied for the prevention of gingivitis and carries.

Originator

Curator's Comment: discovered in 1848 by a Scottish Chemist.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Preventing
Unknown

Approved Use

Unknown
Preventing
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Distinct isoprenoid origins of cis- and trans-zeatin biosyntheses in Arabidopsis.
2004-04-02
Co-expression of three MEP pathway genes and geraniol 10-hydroxylase in internal phloem parenchyma of Catharanthus roseus implicates multicellular translocation of intermediates during the biosynthesis of monoterpene indole alkaloids and isoprenoid-derived primary metabolites.
2004-04
Determination of glycerol by gas chromatography using meso-erythritol as internal standard.
2004-04
The interplay between classical and alternative isoprenoid biosynthesis controls gammadelta T cell bioactivity of Listeria monocytogenes.
2004-03-12
Antagonistic activity of lactic acid bacteria as probiotics against selected bacteria of the Enterobaceriacae family in the presence of polyols and their galactosyl derivatives.
2004-02
Pseudonocardia antarctica sp. nov. an Actinomycetes from McMurdo Dry Valleys, Antarctica.
2004-02
Synthesis of enantiopure 2-C-methyl-D-erythritol 4-phosphate and 2,4-cyclodiphosphate from D-arabitol.
2004-01-08
JAMM: a metalloprotease-like zinc site in the proteasome and signalosome.
2004-01
Distinct light-mediated pathways regulate the biosynthesis and exchange of isoprenoid precursors during Arabidopsis seedling development.
2004-01
Isoprenoid biosynthesis via the MEP pathway. Synthesis of (3,4)-3,4-dihydroxy-5-oxohexylphosphonic acid, an isosteric analogue of 1-deoxy-D-xylulose 5-phosphate, the substrate of the 1-deoxy-D-xylulose 5-phosphate reducto-isomerase.
2003-12-21
Scale-up of erythritol production by an osmophilic mutant of Candida magnoliae.
2003-12
Proteomic analysis of Candida magnoliae strains by two-dimensional gel electrophoresis and mass spectrometry.
2003-12
Sulfonyl-stabilized oxiranyllithium-based approach to polycyclic ethers. Convergent synthesis of the ABCDEF-ring system of yessotoxin and adriatoxin.
2003-11-14
[Properties of 2-C-methyl-D-erythritol 2,4-cyclopyrophosphate--an intermediate in the non-mevalonate isoprenoid biosynthesis].
2003-11-05
Herbaspirillum lusitanum sp. nov., a novel nitrogen-fixing bacterium associated with root nodules of Phaseolus vulgaris.
2003-11
Interactions between metal ions and carbohydrates. Coordination behavior of neutral erythritol to Ca(II) and lanthanide ions.
2003-09-22
An overview of the non-mevalonate pathway for terpenoid biosynthesis in plants.
2003-09
Early steps of deoxyxylulose phosphate pathway in chromoplasts of higher plants.
2003-09
The methylerythritol phosphate pathway and its significance as a novel drug target.
2003-08
A genetic basis for human gammadelta T-cell reactivity towards microbial pathogens.
2003-08
Identification of lethal mutations in Escherichia coli genes encoding enzymes of the methylerythritol phosphate pathway.
2003-07-25
Highly diastereoselective additions to polyhydroxylated pyrrolidine cyclic imines: ready elaboration of aza-sugar scaffolds to create diverse carbohydrate-processing enzyme probes.
2003-07-21
Cross-talk between the cytosolic mevalonate and the plastidial methylerythritol phosphate pathways in tobacco bright yellow-2 cells.
2003-07-18
Adenosine-5'-O-phosphorylated and adenosine-5'-O-phosphorothioylated polyols as strong inhibitors of (symmetrical) and (asymmetrical) dinucleoside tetraphosphatases.
2003-07-15
Glycerol dehydrogenase, encoded by gldB is essential for osmotolerance in Aspergillus nidulans.
2003-07
Biosynthesis of anthecotuloide, an irregular sesquiterpene lactone from Anthemis cotula L. (Asteraceae) via a non-farnesyl diphosphate route.
2003-05-07
Isoprenoid biosynthesis via the methylerythritol phosphate pathway: the (E)-4-hydroxy-3-methylbut-2-enyl diphosphate reductase (LytB/IspH) from Escherichia coli is a [4Fe-4S] protein.
2003-04-24
New quinoproteins in oxidative fermentation.
2003-04-11
Purification and properties of a NADPH-dependent erythrose reductase from the newly isolated Torula corallina.
2003-04-05
Use of the mannitol pathway in fructose fermentation of Oenococcus oeni due to limiting redox regeneration capacity of the ethanol pathway.
2003-04
Maltosyl-erythritol, a major transglycosylation product of erythritol by Bacillus stearothermophilus maltogenic amylase.
2003-03
Functional expression and characterization of EryA, the erythritol kinase of Brucella abortus, and enzymatic synthesis of L-erythritol-4-phosphate.
2003-02-24
The effect of polyol-combinant saliva stimulants on S. mutans levels in plaque and saliva of patients with mental retardation.
2003-02-13
Ustilipids, acylated beta-D-mannopyranosyl D-erythritols from Ustilago maydis and Geotrichum candidum.
2003-02
New developments in oxidative fermentation.
2003-02
Glycosides of 2-C-methyl-D-erythritol from the fruits of anise, coriander and cumin.
2003-01
Liquid formulation of the biocontrol agent Candida sake by modifying water activity or adding protectants.
2003
Sugar metabolism by Brucellae.
2002-12-20
LytB protein catalyzes the terminal step of the 2-C-methyl-D-erythritol-4-phosphate pathway of isoprenoid biosynthesis.
2002-12-18
Mevalonic acid partially restores chloroplast and etioplast development in Arabidopsis lacking the non-mevalonate pathway.
2002-12
Contribution of the mevalonate and methylerythritol phosphate pathways to the biosynthesis of gibberellins in Arabidopsis.
2002-11-22
Isoprenoid biosynthesis through the methylerythritol phosphate pathway: the (E)-4-hydroxy-3-methylbut-2-enyl diphosphate synthase (GcpE) is a [4Fe-4S] protein.
2002-11-15
Elucidation of the methylerythritol phosphate pathway for isoprenoid biosynthesis in bacteria and plastids. A metabolic milestone achieved through genomics.
2002-11
Modeling and measurements of solid-liquid and vapor-liquid equilibria of polyols and carbohydrates in aqueous solution.
2002-09-27
Erythritol attenuates the diabetic oxidative stress through modulating glucose metabolism and lipid peroxidation in streptozotocin-induced diabetic rats.
2002-09-11
Pseudomonas grimontii sp. nov.
2002-09
Isoprenoid biosynthesis via the methylerythritol phosphate pathway. Mechanistic investigations of the 1-deoxy-D-xylulose 5-phosphate reductoisomerase.
2002-09
Sweet elements of Siraitia grosvenori inhibit oxidative modification of low-density lipoprotein.
2002
[Effect of erithriol on intestinal microflora and morphology of rat internal organs].
2002
[Use of a new sugar substitute, erithritol, in the diet therapy of type 2 diabetes patients].
2002
Patents

Sample Use Guides

Patients with type two diabetes mellitus consumed an orange flavored beverage in three separate sessions with a dose of 6, 12 and 18 grams respectively. Endothelial function was assessed before and two hours after consumption by measuring the change in pulse amplitude in response to reactive hyperemia.
Route of Administration: Oral
Biofilms were inoculated with stimulated saliva from healthy donors and grown in a gingivitis model in the continuous presence of 0%, 5%, and 10% erythritol. Biofilms were incubated for 9 days and then analyzed for protease activity, and microbial profile. Biofilm growth was significantly reduced in the presence of erythritol in a dose-dependent manner. Protease activity and the diversity of microbial profiles were also significantly lower. The microbial profile revealed that erythritol induced a compositional shift from periodontitis and gingivitis related taxa toward early colonizers.
Substance Class Chemical
Created
by admin
on Mon Mar 31 17:45:13 GMT 2025
Edited
by admin
on Mon Mar 31 17:45:13 GMT 2025
Record UNII
RA96B954X6
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
E-968
Preferred Name English
ERYTHRITOL
EP   FCC   INCI   MART.   MI   USP-RS   VANDF  
INCI  
Official Name English
Butane 1,2,3,4-tetrol (meso-erythritol)
Common Name English
MESOERYTHRITOL
Systematic Name English
NIK 242
Code English
1,2,3,4-BUTANETETROL, (R*,S*)-
Systematic Name English
MESO-ERYTHRITOL
Common Name English
ERYTHROGLUCIN
Common Name English
ERYTHRITOL [FCC]
Common Name English
Erythritol [WHO-DD]
Common Name English
1,2,3,4-BUTANETETROL
Systematic Name English
FEMA NO. 4819
Code English
ERYTHROL
Common Name English
BUTANE-1,2,3,4-TETROL, (2R,3S)-
Systematic Name English
1,2,3,4-BUTANETETROL, (2R,3S)-REL-
Common Name English
ERYTHRITOL [EP MONOGRAPH]
Common Name English
ERYTHRITOL [MI]
Common Name English
ERYTHRITE
Common Name English
INS NO.968
Code English
TETRAHYDROXYBUTANE
Systematic Name English
ERYTHRITOL [MART.]
Common Name English
F 8015
Code English
NSC-8099
Code English
ZEROSE TM 16957
Common Name English
CARGILL ZEROSE 16957
Common Name English
ERYTHRITOL [VANDF]
Common Name English
INS-968
Code English
ERYTHRITOL [EP IMPURITY]
Common Name English
PHYCITE
Common Name English
ANTIERYTHRITE
Common Name English
ERYTHRITOL [USP-RS]
Common Name English
Classification Tree Code System Code
DSLD 1381 (Number of products:21)
Created by admin on Mon Mar 31 17:45:13 GMT 2025 , Edited by admin on Mon Mar 31 17:45:13 GMT 2025
JECFA EVALUATION INS-968
Created by admin on Mon Mar 31 17:45:13 GMT 2025 , Edited by admin on Mon Mar 31 17:45:13 GMT 2025
CODEX ALIMENTARIUS (GSFA) INS-968
Created by admin on Mon Mar 31 17:45:13 GMT 2025 , Edited by admin on Mon Mar 31 17:45:13 GMT 2025
Code System Code Type Description
CAS
149-32-6
Created by admin on Mon Mar 31 17:45:13 GMT 2025 , Edited by admin on Mon Mar 31 17:45:13 GMT 2025
PRIMARY
MESH
D004896
Created by admin on Mon Mar 31 17:45:13 GMT 2025 , Edited by admin on Mon Mar 31 17:45:13 GMT 2025
PRIMARY
GRAS Notification (GRN No.)
401
Created by admin on Mon Mar 31 17:45:13 GMT 2025 , Edited by admin on Mon Mar 31 17:45:13 GMT 2025
PRIMARY
CHEBI
48299
Created by admin on Mon Mar 31 17:45:13 GMT 2025 , Edited by admin on Mon Mar 31 17:45:13 GMT 2025
PRIMARY
NSC
8099
Created by admin on Mon Mar 31 17:45:13 GMT 2025 , Edited by admin on Mon Mar 31 17:45:13 GMT 2025
PRIMARY
GRAS Notification (GRN No.)
382
Created by admin on Mon Mar 31 17:45:13 GMT 2025 , Edited by admin on Mon Mar 31 17:45:13 GMT 2025
PRIMARY
SMS_ID
100000143030
Created by admin on Mon Mar 31 17:45:13 GMT 2025 , Edited by admin on Mon Mar 31 17:45:13 GMT 2025
PRIMARY
WIKIPEDIA
ERYTHRITOL
Created by admin on Mon Mar 31 17:45:13 GMT 2025 , Edited by admin on Mon Mar 31 17:45:13 GMT 2025
PRIMARY
FDA UNII
RA96B954X6
Created by admin on Mon Mar 31 17:45:13 GMT 2025 , Edited by admin on Mon Mar 31 17:45:13 GMT 2025
PRIMARY
RXCUI
1369563
Created by admin on Mon Mar 31 17:45:13 GMT 2025 , Edited by admin on Mon Mar 31 17:45:13 GMT 2025
PRIMARY RxNorm
EPA CompTox
DTXSID6043919
Created by admin on Mon Mar 31 17:45:13 GMT 2025 , Edited by admin on Mon Mar 31 17:45:13 GMT 2025
PRIMARY
ECHA (EC/EINECS)
205-737-3
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PRIMARY
RS_ITEM_NUM
1241903
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PRIMARY
CHEBI
17113
Created by admin on Mon Mar 31 17:45:13 GMT 2025 , Edited by admin on Mon Mar 31 17:45:13 GMT 2025
PRIMARY
MERCK INDEX
m5003
Created by admin on Mon Mar 31 17:45:13 GMT 2025 , Edited by admin on Mon Mar 31 17:45:13 GMT 2025
PRIMARY Merck Index
DAILYMED
RA96B954X6
Created by admin on Mon Mar 31 17:45:13 GMT 2025 , Edited by admin on Mon Mar 31 17:45:13 GMT 2025
PRIMARY
HSDB
7968
Created by admin on Mon Mar 31 17:45:13 GMT 2025 , Edited by admin on Mon Mar 31 17:45:13 GMT 2025
PRIMARY
GRAS Notification (GRN No.)
789
Created by admin on Mon Mar 31 17:45:13 GMT 2025 , Edited by admin on Mon Mar 31 17:45:13 GMT 2025
PRIMARY
PUBCHEM
222285
Created by admin on Mon Mar 31 17:45:13 GMT 2025 , Edited by admin on Mon Mar 31 17:45:13 GMT 2025
PRIMARY
EVMPD
SUB117926
Created by admin on Mon Mar 31 17:45:13 GMT 2025 , Edited by admin on Mon Mar 31 17:45:13 GMT 2025
PRIMARY
DRUG BANK
DB04481
Created by admin on Mon Mar 31 17:45:13 GMT 2025 , Edited by admin on Mon Mar 31 17:45:13 GMT 2025
PRIMARY
GRAS Notification (GRN No.)
208
Created by admin on Mon Mar 31 17:45:13 GMT 2025 , Edited by admin on Mon Mar 31 17:45:13 GMT 2025
PRIMARY
GRAS Notification (GRN No.)
76
Created by admin on Mon Mar 31 17:45:13 GMT 2025 , Edited by admin on Mon Mar 31 17:45:13 GMT 2025
PRIMARY