HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
D-Pantothensure
PANTOTHENATE · pantothenicacid · Pantothenic · (R)-Pantothenate · (R)-3-(2,4-Dihydroxy-3,3-diMethylbutanaMido)propanoic acid · D-VITAMIN B(5) · Ca pantothenaat · d-pantothenicaci
Identifikatoren & physikalische Daten
| CAS No. | 79-83-4 |
|---|---|
| Summenformel | C9H17NO5 |
| Durchschnittliche Molmasse | 219,23 g/mol |
| Monoisotopische Masse | 219,11067264 g/mol |
| SMILES | CC(C)(CO)[C@@H](O)C(=O)NCCC(=O)O |
| InChIKey | GHOKWGTUZJEAQD-ZETCQYMHSA-N |
| PubChem CID | 6613 |
| ChEMBL | CHEMBL1594 |
| ChEBI | CHEBI:46905 |
| EC No. | 201-229-0 |
| DTXSID | DTXSID9023417 |
| Lokaler Name | D-Pantothensure |
Chemische & physikalische Eigenschaften
| XLogP | -1,1 |
|---|---|
| Polarare Oberfläche (TPSA) | 107 |
| H-Brücken-Donoren | 4 |
| H-Brücken-Akzeptoren | 5 |
| Frei drehbare Bindungen | 6 |
| Schwere Atome | 15 |
| Formalladung | 0 |
| Komplexität | 239 |
| Color/Form | Yellow viscous oilViscous hygroscopic liquid |
| Löslichkeit | SolubleVery soluble in water, benzene, ethyl etherFreely soluble in water, ethyl acetate, dioxane, glacial acetic acidModerately soluble in ether, amyl alcohol. Practically insoluble in benzene, chloroform.1000.0 mg/mLDMSO (Slightly), Methanol (Slightly), Water (Slightly) |
| Decomposition | When heated to decomposition it emits toxic vapors of /nitric oxide/. |
| Schmelzpunkt | 195ºC (D-Calcium Pantothenate salt)MELTING POINT: 170-172 °C /CA SALT/< 25 °C178-179℃ |
| Optical Rotation | Very hygroscopic crystals. Specific optical rotation: + 27.1 deg at 25 °C/D (C = 2) /Pantothenic acid, sodium salt/Minute needles from methyl alcoholsweetish taste with slightly bitter aftertastedecomposes 195-196 °Cmoderately hygroscopic. Specific optical rotation: +28.2 deg at 25 °C/D (c = 5). 1 g dissolves in 2.8 mL water. Soluble in glycerolslightly soluble in alcohol, acetone. pH of 5% aq soln: 7.2 - 8.0pH in CO2-free water: 8.7 /Calcium salt/Specific optical rotation: 37.5 deg at 25 °C/D |
| Physical Description | Viscous liquidUnstable and extremely hygroscopic[Merck Index]Solid |
| Stability/Shelf Life | Unstable ... easily destroyed by acids, bases, heatPantothenoic acid occurs as an unstable, hygroscopic, viscous oil which is freely soluble in water. |
| Collision Cross Section | 151.2 Ų [M+Na]+ [CCS Type: DTBuffer gas: N2Ionization: ESI+Dataset: TOXCASTSource Identifier: DTXSID4047173]147.1 Ų [M-H]- [CCS Type: DTIonization: ESI-146.6 Ų [M-H]- [CCS Type: DTMethod: single field calibrated with ESI Low Concentration Tuning Mix (Agilent)]150.8 Ų [M+Na]+ [CCS Type: DT129.9 Ų [M+H]+ [CCS Type: DT150.17 Ų [M+H]+ [CCS Type: DTMethod: stepped-field]155.27 Ų [M+Na]+ [CCS Type: DT149.87 Ų [M-H]- [CCS Type: DT148.1 Ų [M+H]+ [CCS Type: DTMethod: single field calibrated with Agilent tune mix (Agilent)]145 Ų [M+H]+ [CCS Type: TWMethod: calibrated with polyalanine]203 Ų [M+H]+129.8 Ų [M+H]+ |
| Other Experimental Properties | 1 G EQUALS 70,000-75,000 CHICK UNITSExtremely hygroscopic |
| Siedepunkt | 360.05°C (rough estimate) |
| Dichte | 1.266 |
| Brechungsindex | 1.4315 (estimate) |
| Lagerbedingungen | Sealed in dry,Room Temperature |
| Aggregatzustand | Oil to Gel |
| pKa (Säurekonstante) | 4.30±0.10(Predicted) |
| Farbe | Colourless |
| Stabilität | Hygroscopic |
| Kosmetik-Inhaltsstoffe Funktionen | HAIR CONDITIONINGSKIN CONDITIONINGANTISTATIC |
| InChI | InChI=1/C9H17NO5/c1-9(2,5-11)7(14)8(15)10-4-3-6(12)13/h7,11,14H,3-5H2,1-2H3,(H,10,15)(H,12,13)/t7-/s3 |
| InChIKey | GHOKWGTUZJEAQD-KPOCXSGKNA-N |
| SMILES | [C@H](O)(C(=O)NCCC(=O)O)C(C)(C)CO |&1:0,r| |
| LogP (Verteilungskoeffizient) | -0.856 (est) |
| EPA chemische Informationen | D-Pantothenic acid (79-83-4) |
Sicherheit & Vorschriften
| GHS-Einstufung | This chemical does not meet GHS hazard criteria for 100% (3 of 3) of all reports.Not ClassifiedReported as not meeting GHS hazard criteria by 3 of 3 companies. For more detailed information, please visit ECHA C&L website.Aggregated GHS information provided per 3 reports by companies from 1 notifications to the ECHA C&L Inventory.Reported as not meeting GHS hazard criteria per 3 of 3 reports by companies.There are 0 notifications provided by 0 of 3 reports by companies with hazard statement code(s).Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website. |
|---|---|
| Regulatorische Informationen | Chemical: .beta.-Alanine, N-[(2R)-2,4-dihydroxy-3,3-dimethyl-1-oxobutyl]-.beta.-Alanine, N-(2R)-2,4-dihydroxy-3,3-dimethyl-1-oxobutyl-: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right. |
| Weitere Sicherheitsinformationen | Evaluation - Chemicals that are unlikely to require further regulation to manage risks to environment |
| Gefahrenübersicht | Causes altered sleep time (including change in righting reflex) and somnolence in intraperitoneal lethal-dose studies of mice (LD50 = 1,443 mg/kg)[RTECS] May cause irritation[Sigma-Aldrich MSDS] |
| FDA-Anforderungen | Calcium pantothenate, calcium chloride double salt is a food additive permitted for direct addition to food for human consumption, as long as 1) the quantity of the substance added to food does not exceed the amount reasonably required to accomplish its intended physical, nutritive, or other technical effect in food, and 2) any substance intended for use in or on food is of appropriate food grade and is prepared and handled as a food ingredient. /Calcium pantothenate, calcium chloride double salt/Substance added directly to human food affirmed as generally recognized as safe (GRAS). /Calcium pantothenate/Drug products containing certain active ingredients offered over-the-counter (OTC) for certain uses. A number of active ingredients have been present in OTC drug products for various uses, as described below. However, based on evidence currently available, there are inadequate data to establish general recognition of the safety and effectiveness of these ingredients for the specified uses: pantothenic acid is included in weight control drug products.Sodium pantothenate used as a nutrient and/or dietary supplement in animal drugs, feeds, and related products is generally recognized as safe when used in accordance with good manufacturing or feeding practice. /Sodium pantothenate/ |
| Special Reports | NAS, Food and Nutrition Board, Institute of MedicineDietary Reference Intakes for Thiamin, Riboflavin, Niacin, Vitamin B6, Folate, Vitamin B12, Pantothenic Acid, Biotin, and Choline. National Academy Press, Washington, D.C. (1998).[Available from, as of March 2, 2010: http://www.nap.edu/catalog/6015.html] |
| EPA Safer Chemical | Chemical: Panthothenic acidGreen half-circle - The chemical is expected to be of low concern based on experimental and modeled data. Additional data would strengthen EPA's confidence in the chemical's safer status. |
| Hazard Classes and Categories | Not Classified |
| Entsorgungsverfahren | SRP: Expired or waste pharmaceuticals shall carefully take into consideration applicable DEA, EPA, and FDA regulations. It is not appropriate to dispose by flushing the pharmaceutical down the toilet or discarding to trash. If possible return the pharmaceutical to the manufacturer for proper disposal being careful to properly label and securely package the material. Alternatively, the waste pharmaceutical shall be labeled, securely packaged and transported by a state licensed medical waste contractor to dispose by burial in a licensed hazardous or toxic waste landfill or incinerator.SRP: At the time of review, regulatory criteria for small quantity disposal are subject to significant revision, however, household quantities of waste pharmaceuticals may be managed as follows: Mix with wet cat litter or coffee grounds, double bag in plastic, discard in trash.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. |
| Körperbelastung | The total amount of d-pantothenic acid present in whole blood is estimated to be 1 mg/L in healthy human adults. The liver, adrenal glands, kidneys, brain, and testes contain high concentrations of d-pantothenic acid(1). |
| Wechselwirkungen | Although the clinical importance has not been established, the miotic effects of anticholinesterase ophthalmic preparations (eg, echothiophate iodide (no longer commercially available in the US), isoflurophate) reportedly may be potentiated by pantothenic acid.The hypolipidemic effects of pantothenic acid derivatives (phosphopantothenate, panthenol and pantethine) were studied in mice with hypothalamic obesity ... induced by single injection of aurothioglucose (300 mg/kg body wt, ip). All the tested substances were administered during the last 10 days before decapitation (im, of dosage equivalent to 150 mg/kg body wt of phosphopantothenate). The studied substances inhibited the weight gain of the animals with hypothalamic obesity over the last 10 days of the experiment. The treatment with aurothioglucose increased food intake and mean body weight, blood glucose levelinsulin, serum total cholesterol, triglyceride, the sum of LDL + VLDL and LDL-cholesterol concentrationtriglyceride and cholesterol fractions in the livertriglyceride and FFA content as well as lipoprotein lipase activity in adipose tissue of experimental mice. The administration of the assay compounds lowered food intake and mean body weight, insulin and glucose levels and decreased the content of triglycerides, total cholesterol and cholesterol esters in serum and adipose tissue as well as raised the activity of lipoprotein lipase in adipose tissue and serum lipolytic activity in obese mice. Among the compounds studied the reverse effect of panthenol was especially pronounced. The mechanism of hypolipidemic effects of pantothenic acid derivatives can be related to the reduced resistance to insulin and activation of lipolysis in serum and adipose tissue. /Panthenol, Phosphopantothenate, Pantethine/A combination of 1.2 g of calcium pantothenate, 0.6 g of pyridoxine, 3 g of niacinamide, and 3 g of ascorbic acid taken daily for 6 weeks was associated with elevations in serum transaminase levels in children. One of these doses or the combination may therefore cause hepatotoxicity, but it is not possible from this study alone to ascribe to pantothenic acid the reported adverse effect in liver function.... Pregnant CD-1 mice were administered a teratogenic dose of valproic acid (VPA) prior to neural tube closure and embryonic protein levels were analyzed. ... VPA (400 mg/kg)-induced NTDs (24%) and VPA-exposed embryos with a neural tube defect (NTD) showed a 2-fold increase in p53, and 4-fold decreases in NF-kappaB, Pim-1, and c-Myb protein levels compared to their phenotypically normal littermates (P<0.05). Additionally, VPA increased the ratio of embryonic Bax/Bcl-2 protein levels (P<0.05). Pretreatment of pregnant dams with either folic acid or pantothenic acid prior to VPA significantly protected against VPA-induced NTDs (P<0.05). Folic acid also reduced VPA-induced alterations in p53, NF-kappaB, Pim-1, c-Myb, and Bax/Bcl-2 protein levels, while pantothenic acid prevented VPA-induced alterations in NF-kappaB, Pim-1, and c-Myb...For more Interactions (Complete) data for D-Pantothenic Acid (6 total), please visit the HSDB record page. |
| Lebensmitteluntersuchungswerte | Dietary source of d-pantothenic acid include yeast, chicken, beef, potatoes, oat cereal, vegetables, legumes, and whole grain(1). |
| Unerwünschte Wirkungen | As previously stated, vitamin B5 is considered generally safe. There are no established upper limits since there have been no reports of vitamin B5 toxicity in humans with high intakes. However, there are still side effects involved with the administration of this drug, which include the following.Common Adverse Effects* Muscle pain* Joint pain* Diabetes mellitus, new-onset* Sore throat* Headache* Weakness/lack of energy* Dizziness* Creatine phosphokinase (CPK) elevation* Nausea* Abdominal pain* Alanine transaminase (ALT) elevation* Constipation* Flulike illness* Urinary tract infection (UTI)* Hypersensitivity reactions (including rash, itching, hives, and swelling)* PancreatitisLess Common Adverse Effects* Yellowing skin and eyes (jaundice) |
| Milk Concentrations | Pantothenic acid is excreted in human breast milk with concentration directly proportional to intake. With a dietary intake of 8-15 mg/day, mean milk concentration avg 1.93-2.35 mg/mL. In a group of mothers who had delivered premature babies (26-34 weeks gestational age), pantothenic acid milk levels were significantly > a comparable group with term babies (39-41 weeks). Milk levels in the preterm group avg 3.91 mg/mL up to 40 weeks gestational age and then fell to 3.16 mg/mL. For the term group levels at 2 and 12 weeks postpartum were 2.57 and 2.55 mg/mL, respectively. A 1983 English study measured pantothenic acid levels in pooled human milk obtained from preterm (26 mothers - 29-34 weeks) and term (35 mothers - 39 weeks or longer) patients. Preterm mild rose from 1.29 mg/mL (colostrum) to 2.27 mg/mL (16-196 days), while term milk increased over the same period from 1.26 to 2.61 mg/mL. |
| Toxizitätsübersicht | Safe in the present practices of use and concentration. Ingredient, concentration, and use information are available in documents discoverable at https://cir-reports.cir-safety.orgToxicity is likely at 10,000 mg daily and causes upset stomach and diarrhea as the most common symptoms, according to the National Institutes of Health (NIH) Office of Dietary Supplements. |
| Plant Concentrations | Plants with the highest amount of Pantothenic acid(1). /Pantothenic acid/ [Table#2696] |
| Natural Pollution Sources | Occurs everywhere in animal and plant tissue. The richest common source is liver, but jelly of the queen bee contains 6 times as much as liver. Rice bran and molasses are other good sources.Liver, kidney, yeast, crude molasses, milk, whole-grain cereals, riceHuman milk contains about 2 mg/Lcow's milk, about 3.5 mg/L. Liver and other organ meats and eggs are particularly good sources. Broccoli, cauliflower, white and sweet potatoes, tomatoes and molasses are quite high in pantothenic acid. Muscle tissue of beef, pork, lamb, and chicken are also good sources. |
| Human Toxicity Excerpts | /HUMAN EXPOSURE STUDIES/ Whether high-dose oral contraceptive agents affected pantothenic acid metabolism /was investigated/ in 13 women between the ages of 19 and 24 years enrolled in a 12-day confined study. At the end of the study, blood levels and urinary pantothenic acid excretion were similar in the subjects and controls. The investigators concluded that high-dose oral contraceptive agents do not cause significant changes in the biochemical parameters of pantothenic acid./HUMAN EXPOSURE STUDIES/ The aim of this study was to determine the association between dietary intake, determined using a food frequency questionnaire, and genome damage in lymphocytes measured using the micronucleus (MN) assay. The study, performed on 190 healthy individuals (mean age 47.8 years, 46% males), also examined whether a supplementation with beta-carotene, vitamins C and E along with zinc (ACEZn), in a randomized trial for 6 months, improves genome stability. Multivariate analysis of baseline data showed that (1) the highest tertile of intake of vitamin E, retinol, folic acid, nicotinic acid (preformed) and calcium is associated with significant reductions in MN frequency, i.e. -28, -31, -33, -46 and -49%, respectively (P < 0.005) relative to the lowest tertile of intake and (2) the highest tertile of intake of riboflavin, pantothenic acid and biotin was associated with significant increases in MN frequency, ie +36% (P = 0.054), +51% (P = 0.021), and +65% (P = 0.001), respectively, relative to the lowest tertile of intake. Mid-tertile beta-carotene intake was associated with an 18% reduction in MN frequency (P = 0.038)however, the highest tertile of intake (>6400 ug/day) resulted in an 18% increment in MN frequency. Supplementation with ACEZn significantly reduced the MN index by 13% (P = 0.038). The study also showed interactive additive effects such as the protective effect of increased calcium intake (-46%) and the exacerbating effect of riboflavin (+42%) on increased genome damage caused by low folate intake. The results from this study illustrate the strong impact of a wide variety of micronutrients and their interactions on genome health, depending on the level of intake./HUMAN EXPOSURE STUDIES/ The purpose of this study was to investigate the physiological and performance responses to supplementation with allithiamin and pantethine. On two separate occasions, six highly trained cyclists [maximum O2 consumption or VO2max 61.8 (2.1) mL/kg/min] performed a 50-km steady-state ride on a cycle ergometer at a workload corresponding to approximately 60% of VO2max followed by a 2000-m time trial. For 7 days prior to each ride, subjects daily ingested either a placebo (PL) or a combination of 1 g of allithiamin and 1.8 g of a 55%/45% pantethine/pantothenic acid compound (AP). Treatments were administered using a randomized, double-blind, counter-balanced design. During the 50 km ride, measures of heart rate, respiratory gas exchange and ratings of perceived exertion were recorded at 5, 15, 25, 35 and 45 km. Blood samples were collected at 10, 20, 30, 40 and 50 km and analyzed for lactate, glucose and free fatty acids. Blood samples for the analysis of lactate were also collected 3 and 5 min after the completion of the 2000-m time trial. There were no significant differences in any of the measured parameters between experimental conditions. Time to complete the 2000-m time trial was also not significantly different between experimental conditions [PL 178.2 (8.4), AP 170.7 (10.2) sP=0.58]. These results suggest that, despite the reported enhanced absorption properties, supplementation with allithiamin and pantethine does not alter exercise metabolism or exercise performance./CASE REPORTS/ ... A 76-year-old white woman was admitted to the hospital because of chest pain and dyspnea related to pleurisy and a pericardial tamponade. This patient had no history of allergy and had been taking vitamin B5 and vitamin H for two months. Blood tests performed showed an inflammatory syndrome and a high eosinophil concentration (1200-1500 cells/cu mm). Pleurocentesis and pericardiotomy yielded a sterile exudative fluid with an eosinophilic infiltrate. There were no nuclear antibodies and no rheumatic factorscreenings for viruses, parasites, bacteria, and malignant tumor were negative. A myelogram, biopsy of the iliac crest bone, and concentration of immunoglobulin E were also normal. After withdrawal of the vitamins, the patient recovered and the eosinophilia disappeared. ... This case suggests that vitamin B5 and vitamin H may cause symptomatic, life-threatening, eosinophilic pleuropericarditis. Physicians prescribing these commonly used vitamins should be aware of this potential adverse reaction.For more Human Toxicity Excerpts (Complete) data for D-Pantothenic Acid (7 total), please visit the HSDB record page. |
| Non-Human Toxicity Excerpts | /LABORATORY ANIMALS: Subchronic or Prechronic Exposure/ ... Male rats at 21 d of age were given 0.03% pantothenic acid in their drinking water for 9 weeks. After 9 weeks of treatment, the animals were decapitated, and adrenal cells were cultured in the absence or presence of rat adrenocorticotropic hormone (ACTH10-15 to 10-10 M) and/or ovine prolactin (oPRL10-9 to 10-7 M) for 4 hr. Adrenal cells in pantothenic acid-treated rats exhibited higher basal levels of corticosterone and progesterone than control rats. The response of ACTH and/or PRL on corticosterone and progesterone release was higher in the pantothenic acid-treated rats than in the control rats. In addition, PRL increased the stimulatory effect of ACTH-induced corticosterone secretion in both normal and pantothenic acid-treated rats. These results clearly demonstrated that pantothenic acid supplementation stimulates the ability of adrenal cells in male rats to secrete corticosterone and progesterone. Additionally, these results also showed that pantothenic acid supplementation induced adrenal hyperresponsiveness to ACTH stimulation, and PRL further stimulated adrenal sensitivity to ACTH./OTHER TOXICITY INFORMATION/ Pantothenic acid exhibits no outstanding pharmacodynamic actions following administration to experimental animals ... |
| Probable Routes of Human Exposure | NIOSH (NOES Survey 1981-1983) has statistically estimated that 4,854 workers (52 of these were female) were potentially exposed to d-pantothenic acid in the US(1).NIOSH (NOES Survey 1981-1983) has statistically estimated that 197 workers (52 of these were female) were potentially exposed to sodium pantothenate in the US(1). /Sodium pantothenate/ |
| Antidote and Emergency Treatment | /SRP:/ Immediate first aid: Ensure that adequate decontamination has been carried out. If patient is not breathing, start artificial respiration, preferably with a demand valve resuscitator, bag-valve-mask device, or pocket mask, as trained. Perform CPR if necessary. Immediately flush contaminated eyes with gently flowing water. Do not induce vomiting. If vomiting occurs, lean patient forward or place on the left side (head-down position, if possible) to maintain an open airway and prevent aspiration. Keep patient quiet and maintain normal body temperature. Obtain medical attention. /Poisons A and B//SRP:/ Basic treatment: Establish a patent airway (oropharyngeal or nasopharyngeal airway, if needed). Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with 0.9% saline (NS) during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 mL/kg up to 200 mL of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poisons A and B//SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in severe respiratory distress. Positive-pressure ventilation techniques with a bag valve mask device may be beneficial. Consider drug therapy for pulmonary edema ... . Consider administering a beta agonist such as albuterol for severe bronchospasm ... . Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start IV administration of D5W /SRP: "To keep open", minimal flow rate/. Use 0.9% saline (NS) or lactated Ringer's if signs of hypovolemia are present. For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam or lorazepam ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poisons A and B/ |
| Toxizität | LD50 intraperitoneal in mouse: 1443mg/kg |
| Gefahrstoffdaten | 79-83-4(Hazardous Substances Data) |
Anwendungen & Verwendung
Verwenden
Labelled Pantothenic Acid