meso-エリトリトール

Erythritol

HCID 222285CAS 149-32-6

基本情報

標準SMILES
OC[C@@H](O)[C@@H](O)CO
InChIKey
UNXHWFMMPAWVPI-ZXZARUISSA-N
分子式
C4H10O4
平均分子量
122.12 g/mol
単同位体質量
122.0579088

概要

Erythritol is the meso-diastereomer of butane-1,2,3,4-tetrol. It has a role as an antioxidant, a plant metabolite and a human metabolite.

名称と識別子

優先名称
Erythritol
IUPAC
(2S,3R)-butane-1,2,3,4-tetrol
現地名
meso-エリトリトール
英語名
Erythritol
分子式
C4H10O4
分子量
122.12

名称と別名

ERYTHRITOLmeso-Erythritol149-32-6PhycitolErythritMesoerythritolPhyciteL-Erythritol(2R,3S)-butane-1,2,3,4-tetrolAntierythriteErythroglucin1,2,3,4-Butanetetrol, (2R,3S)-rel-
名称をさらに表示
meso-エリトリトールエリトリトールフィシットL-エリトリトール(2S,3R)-ブタン-1,2,3,4-テトラオール(2R,3S)-1,2,3,4-ブタンテトラオールエリスリトール二ひ酸三コバルト八水和物D-エリトリトールmeso-エリスリトールエリトリットエリスライトmeso-1,2,3,4-ブタンテトラオールエリスリト-ル1,2,3,4-ブタンテトロール2R,3S-1,2,3,4-ブタンテトロールMESO‐エリスリトールMESO-エリトリトール標準品I-エリトリトールmeso-エリトリトール, 99%ERYTHRITE1,2,3,4-BUTANETETROLButanetetrolErythritoD-ErythritolErythritol CRSerythritol,meso-
Payciteerythro-tetritolTetrahydroxybutaneC*Eridex(2S,3R)-butane-1,2,3,4-tetrolDTXSID60439191,2,3,4-Butanetetrol, (R*,S*)-NIK 242

データベース識別子

CAS
149-32-6、7493-90-5
PubChem CID
222285
DTXSID
DTXSID6043919
ChEMBL
CHEMBL349605
ChEBI
CHEBI:17113
UNII
RA96B954X6
EC Number
205-737-3、626-535-5
Nikkaji
J43.360H

物性

構造計算による物性

XLogP
-2.3
極性表面積
80.9 Ų
水素結合供与体数
4
水素結合受容体数
4
回転可能結合数
3
重原子数
8

実験および物理化学的性質

Chemical ClassesOther Uses -> Food Additives
DrugsPharmaceuticals -> Listed in ZINC15
CosmeticsHumectant; Moisturising
SpringerMaterials PropertiesBoiling point
LogP · 2 件

log Kow = -2.29

-2.29

Taste · 2 件

About twice as sweet as sucrose

Compared to sucrose, it exhibits a sweetness of 60-70% depending on the food system

物理化学的性質

融点
118 · 118-120 °C (lit.)
沸点
329 · 329-331 °C (lit.)
比重(密度)
1 · 1,451 g/cm3
屈折率
1.4502 · 1.4502 (estimate)
FEMA
4819 · 4819 | ERYTHRITOL
闪点
329 · 329-331°C
化学的性質 · 2 件

化学的特性Erythritol (meso-erythritol, meso-1,2,3,4-Tetrahydroxybutan) has been known for a long time. Its potential use as a bulk sweetener was, however, recognized rather late. Erythritol is a natural constituent of several foods and beverages in levels sometimes exceeding 1 g/kg. Its solubility in water is approximately 370 g/L at room temperature and increases with increasing temperature. Erythritol melts at 121 C and is stable up to more than 160 C and in a pH range from 2 to 10. Depending on the concentration used, erythritol is approximately 60 % as sweet as sucrose. It is noncariogenic and not metabolized in the human body which means that it is more or less calorie-free. In the European Union, erythritol is approved as E 968 for a large number of food applications. It is GRAS in the United States and also approved in many other countries.

化学性质炭素数が4個の糖アルコールである。カロリーがほぼ0であり,非う性であり,血糖値を上昇させない。

安全と法規制

GHS分類

GHS Classification · 6 件

This chemical does not meet GHS hazard criteria for 98.2% (107 of 109) of all reports.

Not Classified

Aggregated GHS information provided per 109 reports by companies from 4 notifications to the ECHA C&L Inventory.

Warning

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

危険有害性情報

Regulatory Information · 6 件

Chemical: 1,2,3,4-Butanetetrol, (R*,S*)-

Regulation (EC) No 1333/2008 (amended)

1,2,3,4-Butanetetrol, (2R,3S)-rel- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1,2,3,4-Butanetetrol, (2R,3S)-rel- are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

PMN - indicates a commenced PMN (Pre-Manufacture Notices) substance.

Status: Active Update: 31-05-2018 https://echa.europa.eu/registration-dossier/-/registered-dossier/23674

1,2,3,4-Butanetetrol, (2R,3S)-rel-: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationEvaluation - Chemicals that are unlikely to require further regulation to manage risks to environment
Hazards Summary · 1 件

No evidence of reproductive toxicity, developmental toxicity, or teratogenicity in rats or rabbits even at very high doses (10% dietary or 5,000 mg/kg/day intravenously); [REPROTOX] Ingestion of 50 grams can cause nausea and mild GI discomfort; [Reference #1] May cause irritation; [Sigma-Aldrich MSDS]

FDA Requirements · 1 件

Food labeling. Health claims: dietary noncariogenic carbohydrate sweeteners and dental caries. ... Eligible noncariogenic carbohydrate sweeteners are the sugar alcohols xylitol, sorbitol, mannitol, maltitol, isomalt, lactitol, hydrogenated starch hydrolysates, hydrogenated glucose syrups, and erythritol, or a combination of these.

Hazard Classes and Categories · 2 件

Not Classified

Skin Irrit. 2 (100%)

Hazardous Reactivities and IncompatibilitiesErythritol is incompatible with strong oxidizing agents and strong bases.

安全と保護具

Fire Fighting Procedures · 2 件

Water spray, dry chemical, carbon dioxide or foam as appropriate for surrounding fire and materials.

This material is assumed to be combustible. As with all dry powders it is advisable to ground mechanical equipment in contact with dry material to dissipate the potential buildup of static electricity.

Storage Conditions · 2 件

Store in tight container as defined in the USP-NF. This material should be handled and stored per label instructions to ensure product integrity. Store in a refrigerator.

When stored for up to 4 years in ambient conditions (20 °C, 50% RH) erythritol has been shown to be stable.

Cleanup Methods · 1 件

Wear approved respiratory protection, chemically compatible gloves and protective clothing. Wipe up spillage or collect spillage using a high efficiency vacuum cleaner. Avoid breathing dust. Place spillage in appropriately labeled container for disposal. Wash spill site.

Disposal Methods · 1 件

SRP: Criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Preventive Measures · 3 件

As with all fires, evacuate personnel to a safe area. Firefighters should use self-contained breathing equipment and protective clothing.

As a general rule, when handling USP Reference Standards avoid all contact and inhalation of dust, mists, and/or vapors associated with the material. Wash thoroughly after handling.

/Wear/ chemically compatible gloves, /and/ safety glasses or goggles. Protect exposed skin.

Personal Protective Equipment (PPE) · 2 件

Engineering controls such as exhaust ventilation are recommended.

Use a NIOSH approved respirator, if it is determined to be necessary by an industrial hygiene survey involving air monitoring. In the event that a respirator is not required, an approved dust mask should be used.

毒性情報

Body Burden · 2 件

Erythritol ... can ... be found in the human body.

Seven polyols, erythritol, arabinitol, anhydroflucitol, mannitol, sorbitol, myoinositol and possibly ribitol were identified in human cerebrospinal fluid by means of gas-liquid chromatography and mass spectrometry. Quantitative data were obtained for five polyols, arabinitol, anhydroglucitol, mannitol, sorbitol and myoinositol, by screening of 205 CSF samples. These five polyols represented 90-95 per cent of the polyol-concentration which was 340 +/- 105 mumol/1 in the total series. The concentration of polyols in the CSF was two times higher than that in the plasma (148 +/- 30 mumol/1), where only anhydroglucitol and myoinositol could be quantitated. The variations noted were not associated with age, sex or the plasma concentrations of polyols. The polyols of the CSF most likely originate from brain tissue and/or spinal cord since penetration from the plasma against a gradient seems unlikely.

Environmental Fate · 3 件

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 1(SRC), determined from a structure estimation method(2), indicates that erythritol is expected to have very high mobility in soil(SRC). Volatilization of erythritol from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 3.1X10-10 atm-cu m/mole(SRC), using a fragment constant estimation method(3). Erythritol is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 5.2X10-7 mm Hg at 25 °C(SRC), determined from a fragment constant method(4). Biodegradation data in soil were not available(SRC, 2011).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 1(SRC), determined from a structure estimation method(2), indicates that erythritol is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 3.1X10-10 atm-cu m/mole(SRC), developed using a fragment constant estimation method(4). According to a classification scheme(5), an estimated BCF of 3(SRC), from its log Kow of -2.29(6) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Biodegradation data in water were not available(SRC, 2011).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), erythritol, which has an estimated vapor pressure of 5.2X10-7 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase erythritol is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 4 hours(SRC), calculated from its rate constant of 2.9X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase erythritol may be removed from the air by wet or dry deposition(SRC). Erythritol does not contain chromophores that absorb at wavelengths >290 nm(4), and therefore is not expected to be susceptible to direct photolysis by sunlight(SRC).

Soil Adsorption/Mobility · 1 件

Using a structure estimation method based on molecular connectivity indices(1), the Koc of erythritol can be estimated to be 1(SRC). According to a classification scheme(2), this estimated Koc value suggests that erythritol is expected to have very high mobility in soil.

Natural Pollution SourcesErythritol ... is present in various fruits, vegetables, and fermented fruits.
Human Toxicity Excerpts · 5 件

/HUMAN EXPOSURE STUDIES/ In order to investigate the effects of repeated doses of erythritol on blood glucose control and renal function in patients with non-insulin-dependent diabetes mellitus, three male out-patients (mean age, 65 +/- 6 years) and eight female out-patients (mean age, 50 +/- 14 years) consumed 20 g of erythritol in a solution throughout the day daily for 14 days with their usual diet, but without specific restriction on timing or division of the daily dose. Food intake was monitored for three days before the test and three days before the end of the test. Body weights before and after administration and blood glucose and hemoglobin A1c after fasting were determined in all participants as indices of control of diabetes. In four or five of the subjects, blood urea nitrogen, creatinine, beta-2-microglobulin, and urinary proteins (not specified) were measured as indices of renal function before and after erythritol treatment. None of the participants reported diarrhea or any other subjective symptoms during treatment. The blood glucose concentrations after fasting, reported for nine subjects (sex not specified), decreased from 181 +/- 60 mg/dL before administration to 165 +/- 57 mg/dL after administration, which was not significant. The hemoglobin A1c concentrations after fasting, reported for all 11 participants, were the same as those before treatment for four, decreased in six, and increased in one subject after erythritol treatment. The large decreases in two subjects resulted in a decrease in the group mean value after treatment, to 7.5 +/- 1.6% from 8.5 +/- 1.5% before administration. Blood urea nitrogen, creatinine, and beta -2-microglobulin values were reported for only five or fewer subjects, but erythritol had no effect on these parameters. Urinary proteins, as measured colorimetrically for an unspecified number of participants, were reported not to be affected by erythritol treatment. ...

/HUMAN EXPOSURE STUDIES/ The gastrointestinal tolerance and diuretic response to repeated doses of erythritol were examined in a double-blind, two-way cross-over study in which healthy men consumed erythritol and, for comparison, sucrose. Twelve men aged 22-46 and weighing 65-98 kg consumed each test material for seven days, comprising a two-day adaption period at home and a five-day test period under supervision. The men consumed 0.3 g/kg bw erythritol or 0.6 g/kg bw sucrose in test foods during the first and second day of adaptation, respectively, and 1 g/kg bw per day of erythritol or sucrose in yoghurt, biscuits, soft drinks, or chocolate under supervision. In order to attain the correct dose, fixed amounts were given in test foods at each meal except the evening meal, when individual doses of the test compounds were administered in order to reach the nominal dose of 1 g/kg bw for each subject. Beverages such as mineral water and fruit juice were allowed ad libitum, but consumption of caffeine-containing drinks was limited to four cups per day. ... The entire urine volume was collected at five 3-hr intervals during the day and one 9-hr interval overnight throughout the test period, and sodium, potassium, chlorine, calcium, phosphorus, citrate, gamma-glutamyl transpeptidase and N-acetylglucosamine activities, beta-2-microglobulin, urea, and creatinine were determined. The concentration of erythritol was determined in a separate aliquot. The daily dose 1 g/kg bw per day erythritol was well tolerated, with no increase in the reported incidence of gastrointestinal symptoms such as flatulence, abdominal cramps, and diarrhea. One man reported thirst during treatment with erythritol, but there were no differences in the subjective judgements of the frequency and quantity of urine production. Fluid intake varied considerably among the study participants, from 800 to 6600 mL/man per day, and the averages for both treatment periods were reported to be high in comparison to usual intakes, but there was no significant difference between the two periods. Urine production was about 7% higher during erythritol treatment, but the increase was not statistically significant. Urinary excretion of erythritol resulted in significantly (p < 0.001) increased urine osmolarity and hourly output of osmotically active solutes, but urinary pH and the excretion of creatinine, urea, citrate, sodium, potassium, and chlorine were not affected. Marginal but statistically significant increases in calcium concentration, microalbumin, beta-2-microglobulin, and N-acetylglucosamine activity were noted consistently over the five-day period after ingestion of erythritol, although the values for these parameters remained within reference intervals and below values that would be considered clinically relevant. The data on gamma-glutamyl transpeptidase activity were considered unreliable and were therefore not reported. Thus, 1 g/kg bw of erythritol was consumed as part of the regular diet over five days without adverse gastrointestinal symptoms. Urine volume and urinary electrolyte and protein excretion were not significantly affected at this dose, suggesting the absence of a diuretic effect, although the high fluid consumption of the participants and the consumption of coffee and/or tea (up to four cups per day) may have prevented the detection of any diuretic effect of erythritol.

/HUMAN EXPOSURE STUDIES/ In a study of the gastrointestinal tolerance of healthy adults to repeated ingestion of a tea drink containing erythritol, eight male volunteers aged 30-53 years, with a mean body weight of 70 kg, consumed five tins of tea drink, one after each meal and two between meals, for three consecutive days, for a total of 60 g erythritol and an average intake of 0.86 g/kg bw per day. Each subject completed a questionnaire on his general condition, including stool consistency and abdominal condition after ingestion. Effects on urine volume were not evaluated. No changes in stool consistency or on the frequency of defecation were reported, and no adverse effects on gastrointestinal condition or general health were reported.

/HUMAN EXPOSURE STUDIES/ The gastrointestinal tolerance of healthy adults to repeated ingestion of a coffee drink containing erythritol was evaluated in six male volunteers aged 30-53 years and with a mean body weight of 74 kg. The men drank five tins of coffee drink, one after each meal and two between meals, for three consecutive days, for a total quantity of erythritol ingested of 68 g and an average intake of 0.91 g/kg bw per day. Each man completed a questionnaire on his general condition, including stool consistency and abdominal condition after ingestion. Effects on urine volume were not evaluated. No changes in stool consistency or on the frequency of defecation were reported, and no abdominal symptoms were observed. Three of the men reported dryness or irritation of the throat and/or stomach, which was resolved by drinking water. The author suggested that these symptoms were due to the high osmotic activity of the coffee drink.

For more Human Toxicity Excerpts (Complete) data for Erythritol (14 total), please visit the HSDB record page.

Artificial Pollution SourcesErythritol's production and use as a non-nutritive sweetener in beverages(1) may result in its release to the environment through various waste streams(SRC).

法規制情報

FDA Requirements · 1 件

Food labeling. Health claims: dietary noncariogenic carbohydrate sweeteners and dental caries. ... Eligible noncariogenic carbohydrate sweeteners are the sugar alcohols xylitol, sorbitol, mannitol, maltitol, isomalt, lactitol, hydrogenated starch hydrolysates, hydrogenated glucose syrups, and erythritol, or a combination of these.

安全データ

F
3-10
wgk
3
tsca
TSCA listed
rtecs
KF2000000
毒性
LD50 in male, female rats (g/kg): 6.6, 9.6 i.v.; >16, >16 s.c.; 13.1, 13.5 orally (Munro)
hs_code
29054910

化学と産業

薬理情報

Mechanism of Action · 2 件

... Reports from authoritative bodies and reviews indicates that the decrease in pH in plaque as a consequence of metabolic acid production by saccharolytic bacteria when exposed to fermentable carbohydrates (i.e. sugars and starches) may promote demineralization and prevent remineralization of the hydroxyapatite crystals. Tooth hydroxyapatite crystals are very resistant to dissolution at neutral pH, but their solubility drastically increases as pH drops. Typically, the critical pH for dental enamel is around 5.5. ... Demineralization of tooth tissues can also occur as a result of consumption of dietary acids in foods or beverages, and that frequent consumption can lead to dental erosion. Xylitol, sorbitol, mannitol, maltitol, lactitol, isomalt, erythritol, D-tagatose, isomaltulose, sucralose and polydextrose are slowly metabolized by bacteria in the mouth. The rate and amount of acid production from these food constituents is significantly less than that from sucrose. ... Xylitol, sorbitol, mannitol, maltitol, lactitol, isomalt, erythritol, D-tagatose, isomaltulose, sucralose and polydextrose do not promote dental caries because they do not lower plaque pH to the level associated with enamel demineralization. ... A cause and effect relationship has been established between the consumption of sugar-containing foods/drinks at an exposure frequency of four times daily or more and an increased tooth demineralization, and that the consumption of foods/drinks containing xylitol, sorbitol, mannitol, maltitol, lactitol, isomalt, erythritol, D-tagatose, isomaltulose, sucralose or polydextrose, instead of sugar in sugar-containing foods/drinks, may maintain tooth mineralization by decreasing tooth demineralization compared with sugar-containing foods, provided that such foods/drinks do not lead to dental erosion.

The food constituents xylitol, sorbitol, mannitol, maltitol, lactitol, isomalt, erythritol, D-tagatose, isomaltulose, sucralose or polydextrose resulted in reduced post-prandial blood glucose (or insulinemic) responses compared with sugars on a weight by weight basis owing to their reduced/delayed digestion/absorption and/or to a decrease in the amount of available carbohydrates, and that the consumption of foods/drinks in which xylitol, sorbitol, mannitol, maltitol, lactitol, isomalt, erythritol, D-tagatose, isomaltulose, sucralose or polydextrose replaced sugars induced lower post-prandial glycaemic and insulinaemic responses than sugar-containing foods/drinks. ... A cause and effect relationship has been established between the consumption of foods/drinks containing xylitol, sorbitol, mannitol, maltitol, lactitol, isomalt, erythritol, D-tagatose, isomaltulose, sucralose or polydextrose instead of sugar and reduction in post-prandial blood glucose responses (without disproportionally increasing post-prandial insulinemic responses) as compared to sugar-containing foods/drinks.

Biological Half-Life · 3 件

After a 12 hr fast, five men received a single oral dose of 0.3 g/kg bw erythritol as a 20% aqueous solution. Urine samples were collected over 48 hr and blood samples over 24 hr to allow determination of erythritol. The compound appeared to be readily absorbed, the plasma concentration peaking at 430 g/mL 30 min after treatment, with a half-time of 3.4 hr. ...

Three beagle dogs were given a single oral dose of 1 g/kg bw (14)C-erythritol after an 18 hr fast and were then housed individually in metabolism cages and fasted for an additional 8 hr. Blood samples were collected from each dog 1, 5, 15, and 30 min and 1, 2, 3, 4, 5, 6, 8, 24, 48, 72, 96, and 120 hr after dosing for determination of radiolabel in blood and plasma and for calculation of the ratio of distribution to erythrocytes. ... The concentration of erythritol in blood and plasma reached a peak 30 min after dosing and decreased in a biphasic manner with half-times of 0.07 and 1.7 hr in blood and 0.5 and 5.4 hr in plasma. ...

Groups of three male Wistar rats were given a single oral dose of 0.125, 0.25, 0.5, 1, or 2 g (14)C-erythritol/kg bw after an 18 hr fast, and they were fasted for an additional 8 hr after dosing. Blood samples were collected from the tail vein 15 and 30 min and 1, 2, 4, 6, 8, 12, 24, 48, and 72 hr after dosing in order to measure radioactivity. ... After the initial absorption, a biphasic decrease in the blood concentration of radiolabel was seen, with half-time values for the biphasic decrease of about 2 and 20 hr, respectively. The biphasic decrease was also observed at 2 g/kg bw, but the half-time values were longer (3 and 28 hr), indicating a slower rate of elimination. ...

Metabolism/Metabolites · 3 件

In studies designed to investigate the metabolism of erythritol in vivo in healthy volunteers and to compare the fermentation of erythritol by human fecal flora in vitro with that of glucose and lactitol, four male and two female volunteers aged 21-25 undertook an overnight fast and were then chosen at random to receive a single dose of 25 g (13)C-erythritol, (13)C-glucose, and (13)C-lactitol in 250 mL of water with at least three days between each treatment. Breath samples were taken for analysis of (13)C-carbon dioxide and hydrogen gas before treatment and at 30 min intervals up to 6 hr after treatment. The ratio of (13)C:(12)C-carbon dioxide was measured by isotope-ratio mass spectrometry. ... In order to maintain a constant metabolic rate, the subjects remained at rest during the study. For the assay of fermentation in vitro, fecal samples were collected from six healthy volunteers (sex and age not specified) who ate a normal western diet. None of the subjects complained of gastrointestinal symptomsand none had used antibiotics in the past six months. The samples were incubated under anaerobic conditions for 6 hr, and then the hydrogen gas concentration was measured in the head-space of the incubation vials. ... After a 6 hr incubation with erythritol, the amount of hydrogen gas formed by the fecal flora was comparable to that in control vials, but significantly (p < 0.001) more hydrogen gas was produced in the glucose and lactitol vials than in either control or erythritol.

Groups of three Wistar rats of each sex were given a single dose of 0.1 g/kg bw (14)C-erythritol by gavage, as follows: germ-free rats were kept under sterile conditions until administration of commercial (14)C-erythritol; adapted conventional rats received diets containing weekly increases of 5, 10, and 20% erythritol for three weeks before administration of commercial (14)C-erythritol; unadapted conventional rats were kept on CIVO stock diet before administration of commercial (14)C-erythritol; or germ-free rats were kept under sterile conditions until dosing with purified (14)C-erythritol. Rats were not fasted before dosing. Immediately after treatment, the rats were placed in individual metabolism cages to allow collection of expired carbon dioxide, urine, and feces over 24 hrs. ... In rats that received commercial (14)C-erythritol, 2.5-2.9% of the radiolabel was erythrose and 0.2-0.35% was glucose. In germ-free rats that received purified (14)C-erythritol, less radiolabel was associated with erythrose. No volatile radioactive components were identified by lyophilization of the urine samples.

Groups of 11 male Wistar rats were fed control diet or control diet containing 10% erythritol (added at the expense of corn starch) for two weeks. They were then sacrificed, the caecal contents were collected and pooled by group, and the contents were suspended. Samples of each suspension were incubated with 12 mg (14)C-erythritol (10 uCi) for 6 hr under anaerobic conditions, and the incubation mixture was analyzed for erythritol, short-chain fatty acids, and carbon dioxide 1, 2, 4, and 6 hr after the beginning of incubation. The total recoveries of radiolabel were comparable for control and treated groups at the end of incubation, but the proportions of all (14)C-labelled products of fermentation differed significantly ( p < 0.01) between the two groups: in the controls, 84% of the radiolabel was present as unchanged erythritol, and carbon dioxide, acetic acid, propionic acid, and butyric acid each accounted for < 2% of the radiolabel; in contrast, < 1% of the radiolabel in the caecal contents of treated rats was present as erythritol at the end of incubation, 17% of the administered dose was released as (14)C-carbon dioxide within 2 hr of incubation, and 24% of the radiolabel was recovered as (14)C-carbon dioxide by the end of the incubation period. Succinic, acetic, propionic, and butyric acids were identified as fermentation products and accounted for about 60% of the radiolabel at the end of the incubation period. Succinic acid was detectable after 1 hr but not subsequently, suggesting that it was fermented to other products.

MeSH Pharmacological ClassificationDrugs used to cause dilation of the blood vessels.
Absorption, Distribution and Excretion · 5 件

In 12 male subjects who consumed 1 g/kg bw per day erythritol in a variety of foods during a five-day test period under controlled conditions, the mean urinary excretion was 61-88% of the nominal ingested dose, with an average of 78%.

The peak serum concentration of erythritol in five non-insulin-dependent diabetic patients (sex not indicated) who consumed a single dose of 20 g erythritol in solution occurred 1 hr after administration and was 650 +/= 37 ug/mL. On average, 82, 88, and 88% of the administered erythritol was recovered in the urine 24, 48, and 72 hrs after dosing, respectively.

After 12 male and 12 female volunteers received a dose of 0.4 or 0.8 g/kg bw erythritol in a chocolate snack, the plasma erythritol concentrations increased rapidly, reaching peaks of 3 and 5 mmol/L 1 and 2 hrs after dosing with 0.4 and 0.8 g/kg bw, respectively. Starting 2 hrs after treatment, the plasma erythritol concentrations were significantly (p < 0.05) higher in the group given 0.8 g/kg bw than in that given 0.4 g/kg bw. At both doses, erythritol appeared in the urine within 2 hrs of dosing, the largest quantities being collected between 2 and 4 hrs after administration. Erythritol was still present in urine 22 hrs after treatment. The concentration of erythritol in the urine of individuals given 0.8 g/kg bw was about twice and significantly (p < 0.05) greater than that in the urine of people given 0.4 g/kg bw. On average, 61 and 62% of the administered erythritol was recovered in the urine after the 0.4 and 0.8 g/kg bw doses, respectively, within 22 hrs.

The kinetics of erythritol in plasma and urine were investigated in three men and three women after an overnight fast. Each subject ingested a single oral dose of 1 g/kg bw dissolved in 250 mL of water, and blood samples were taken 5, 10, 15, 30, 45, 60, 90, 120, 180, and 240 min after dosing for determination of plasma concentrations of erythritol. Plasma creatinine concentrations were determined in a blood sample taken before treatment. Urine was collected over 0-30 min, 30-60 min, 1-2 hr, 2-3 hr, and 3-24 hr after treatment for determination of the volume and of the erythritol and creatinine concentrations. Erythritol was detected in the plasma 10 min after dosing, and the mean plasma concentrations increased steadily from 15 min after treatment to a peak of 2.2 mg/mL after 90 min. The urine volume and erythritol concentration reached a maximum during 1-2 hr after ingestion, at about the same time that the plasma concentration of erythritol peaked. Urinary recovery of erythritol over the 24 hr collection period accounted for 78% of the administered dose, with 30% collected after 3 hr. During 1 and 2 hr after administration, the clearance of erythritol was about half that of creatinine, indicating tubular reabsorption of erythritol by the kidney.

For more Absorption, Distribution and Excretion (Complete) data for Erythritol (20 total), please visit the HSDB record page.

Tissue LocationsEpidermis

用途と製造

Uses · 4 件

Occurs naturally in fruits and fermented foods; Used as a food additive (non-nutritive sweetener); [Merck Index] Used in pharmaceuticals and to make erythrityl tetranitrate; [HSDB] Used as a flavor enhancer, humectant, carrier, and sweetener for foods; [JECFA]

Erythritol is a naturally occurring noncariogenic excipient used in a variety of pharmaceutical preparations, including in solid dosage forms as a tablet filler, and in coatings. It has also been investigated for use in dry powder inhalers. It is also used in sugar-free lozenges, and medicated chewing gum.

Non-nutritive sweetener in beverages

Manufacture of erythrityl tetranitrate

U.S. Production2022: 167,551 lb
Consumer UsesNot Known or Reasonably Ascertainable
Industry UsesNot Known or Reasonably Ascertainable
Methods of Manufacturing · 1 件

Erythritol is produced on industrial scale by fermentation. ... As starting material, aqueous solutions of glucose or sucrose are used. The naturally occurring yeast Moniliella pollinis, originally isolated from pollen found in a honeycomb, is used for the fermentation. In the fermentation broth, large amounts of erythritol are formed besides other polyols. After filtration, ion exchange chromatography, and concentration, erythritol is crystallized with more than 99% purity.

Household ProductsInformation on 3 consumer products that contain Erythritol in the following categories is provided:
応用分野 · 6 件

解説1,2,3,4-butanetetrol.C4H10O4(122.12).トレオースの糖アルコール.D-,L-トレイトールの2種類の異性体がある.D-トレイトールはジュートやキマメの樹皮,枝,葉に含まれる."融点88 ℃.[α]D"+4.6°(水).L-トレイトールはL-トレオースの還元によって得られる.融点72~74 ℃.[α]D"-4.0°(水).DL-トレイトールは融点72 ℃.いずれも硝酸で強く酸化すると対応する酒石酸を与える.[CAS 7493-90-5][CAS 6968-16-7:DL-トレイトール]森北出版「化学辞典(第2版)

用途エリスリトールは糖アルコールに分類される甘味料で、果実やキノコの他、ワイン?清酒などの発酵食品に含まれている天然の糖質です。

用途糖研究用、甘味料研究用。

使用Erythritol is a sweetener (polyol) manufactured by fermentation of glucose, the glucose-rich substrate being obtained by the enzymatic hydrolysis of starch. it is 60–70% as sweet as sugar, has excellent heat and acid stability, a high digestive tolerance, and a caloric value of 0.2 kcal/g. it is the only polyol produced by fermentation. it can be used as a sugar replacement in confectioneries, beverages, and desserts.

一般的な説明meso-Erythritol, belonging to the class of sugar alcohols, is identified in a variety of food products, fruits, vegetables, beverages and dietary supplements. It is known as a low glycemic food additive and plays an important role as a sweetener for diabetic patients, since it does not have glycemic or insulinemic effect due to its ability to not get metabolized but get absorbed in the small intestine. It is also reportedly used as a sugar substitute in toothpaste, chewing gums, confectionery food products, etc.

使用用途エリスリトールにはカロリーがほとんどなく、砂糖と置き換えると、肥満や血糖値の低減に効果的です。そのため、主に砂糖の代替甘味料として使用されています。 エリスリトールを含む一般的な食品の例に、キャンディ、ガム、清涼飲料水などが挙げられます。特定健康食品として虫歯の発生低減を目的に使用されたり、糖尿病患者等、病者用食品の甘味料として利用可能です。 さらに、放熱効果があるため、化粧品成分として化粧水など、保湿調整にも用いられています。

調製方法 · 3 件

Erythritol is a starch-derived product. The starch is enzymatically hydrolyzed into glucose which is turned into erythritol via a fermentation process, using osmophilic yeasts or fungi (e.g. Moniliella pollinis, or Trichosporonoides megachiliensis).

合成方法化学合成法では金属触媒を用い,デンプンを高温条件下で反応させることにより合成可能。工業的にはグルコースやスクロースを原料とし,酵母Aureobasidiumなどの発酵により生産されている。

純化方法meso-Erythritol crystallises from distilled water or absolute EtOH and is dried at 60o in a vacuum oven. It sublimes at 110o in a high vacuum. It is optically inactive. [Jeans & Hudson J Org Chem 20 1565 1955, IR: Kuhn Anal Chem 22 276 1950, Beilstein 1 IV 2807.]

上流・下流製品情報

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補足説明

定義本品は、次の化学式で表される四価アルコールである。

定義ChEBI: Erythritol is the meso-diastereomer of butane-1,2,3,4-tetrol. It has a role as an antioxidant, a plant metabolite and a human metabolite.

関連反応

37 件

関連ノート

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