DL-乳酸

Lactic Acid

HCID 612CAS 26100-51-6

基本信息

标准SMILES
CC(O)C(=O)O
InChIKey
JVTAAEKCZFNVCJ-UHFFFAOYSA-N
分子式
C3H6O3
平均分子量
90.08 g/mol
单同位素质量
90.03169405

概述

Lactic acid appears as a colorless to yellow odorless syrupy liquid. Corrosive to metals and tissue. Used to make cultured dairy products, as a food preservative, and to make chemicals.

名称与标识

首选名称
Lactic Acid
IUPAC
2-hydroxypropanoic acid
英文名
Lactic acid
分子式
C3H6O3
分子量
90.07794

名称与别名

lactic acid2-hydroxypropanoic acidDL-Lactic acid50-21-52-hydroxypropionic acidMilk acidTonsillosanRacemic lactic acidOrdinary lactic acidAcidum lacticumEthylidenelactic acidLactovagan
展开更多名称
MilchsaeureLactic acid, dl-Kyselina mlecnaLacticum acidumPropanoic acid, 2-hydroxy-598-82-3alpha-Hydroxypropionic acidLactic acid USP

数据库标识

CAS
26100-51-6、50-21-5、598-82-3
PubChem CID
612
DTXSID
DTXSID7023192
ChEMBL
CHEMBL1200559
ChEBI
CHEBI:78320
UNII
3B8D35Y7S4
EC Number
200-018-0、209-954-4、825-250-5
Nikkaji
J1.358G

性质

结构计算性质

XLogP
-0.7
极性表面积
57.5 Ų
氢键供体
2
氢键受体
3
可旋转键
1
重原子
6

实验与物化性质

Chemical ClassesOther Classes -> Organic Acids
Cosmetics · 2 条

Cosmetic ingredients (Lactic Acid) -> CIR (Cosmetic Ingredient Review)

Skin conditioning; Humectant; Buffering

pHThe pH of a 10 wt% aqueous solution of lactic acid is 1.75
FragrancesFragrance Ingredient (Lactic acid) -> IFRA transparency List
Pesticides · 2 条

Plant Growth Regulators

Active substance -> EU Pesticides database: Not approved

LogP · 3 条

log Kow = -0.72

-0.6

-0.62

安全与法规

GHS分类

GHS Classification · 6 条

This chemical does not meet GHS hazard criteria for 0.2% (5 of 2808) of reports.

Danger

H314 (11.8%): Causes severe skin burns and eye damage [Danger Skin corrosion/irritation]

P260, P264, P264+P265, P280, P301+P330+P331, P302+P352, P302+P361+P354, P304+P340, P305+P354+P338, P316, P317, P321, P332+P317, P362+P364, P363, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 2808 reports by companies from 35 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Danger

危害信息

Regulatory Information · 6 条

Chemical: Propanoic acid, 2-hydroxy-

Regulation (EC) No 178/2002 (amended)

Propanoic acid, 2-hydroxy- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Propanoic acid, 2-hydroxy- 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)

2004/129/EC

Status: Active Update: 04-01-2023 https://echa.europa.eu/registration-dossier/-/registered-dossier/5165

Lactic acid: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationEvaluation - Lactic acid isomers
DOT LabelCorrosive
Fire Hazards · 2 条

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:

Combustible.

Health Hazards · 1 条

Inhalation of mist causes coughing and irritation of mucous membranes. Ingestion, even of diluted preparations, has a corrosive effect on the esophagus and stomach. Contact with more concentrated solutions can cause severe burns of skin or eye. (USCG, 1999)

Hazards Summary · 1 条

Corrosive to skin; [Quick CPC] A skin and respiratory tract irritant; Corrosive to eyes; [ICSC] Causes burns to skin and eyes; Vapors cause eye and mucous membrane irritation and can cause coughing and difficulty breathing; [CHRIS] Safe when used as a flavoring agent in food; [JECFA] Corrosive to rabbit skin, mildly irritating to guinea pig skin, and not irritating to pig skin; Not sensitizing in a study of guinea pigs; A 13-week oral study of rats produced a NOAEL of 500 mg/kg/day (highest tested dose); Studies on reproductive and developmental toxicity not considered necessary because lactic acid is a product of human intermediary metabolism; [EPA ChAMP] A skin and strong eye irritant; [Aldrich MSDS]

安全与防护

Fire Fighting · 2 条

Excerpt from ERG Guide 153 [Substances - Toxic and/or Corrosive (Combustible)]:

Use water spray, powder, alcohol-resistant foam, carbon dioxide.

First Aid Measures · 4 条

Fresh air, rest. Refer for medical attention.

Remove contaminated clothes. Rinse skin with plenty of water or shower.

First rinse with plenty of water for several minutes (remove contact lenses if easily possible), then refer for medical attention.

Rinse mouth. Do NOT induce vomiting. Give nothing to drink. Refer for medical attention .

First AidINHALATION: move to fresh air.
Safe StorageSeparated from strong bases.
Fire Fighting Procedures · 2 条

Suitable extinguishing media: Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.

Advice for firefighters: Wear self-contained breathing apparatus for firefighting if necessary.

Storage Conditions · 3 条

Keep container tightly closed in a dry and well-ventilated place. Containers which are opened must be carefully resealed and kept upright to prevent leakage. Hygroscopic.

Separated from strong bases.

When heated to decomposition it emits acrid smoke and irritating fumes.

毒理信息

Body BurdenLactic acid was found to be excreted by humans through urine at a rate of 40 mg/kg body weight/day and through sweat at 45-452 mg/100 mL(1).
Interactions · 5 条

The effects of local myocardial administration of lactic acid and low-dose edaravone were investigated to determine if this combination provides benefits similar to mechanical postconditioning. We randomly divided 108 rats into 6 groups: sham, reperfusion injury, postconditioning (Post), lacticacid (Lac), low-dose edaravone (Eda), and lactic acid + low-dose edaravone (Lac+Eda). The left coronary arteries of the rats were occluded for 45 minutes, before the administration of the treatments. The rats were euthanized at different time points to examine the infarct size and serum markers of myocardial injury and apoptosis and measure the expression of signal pathway markers. We found that the infarct areas caused by ischemic-reperfusion injury were reduced largely by postconditioning and Lac+Eda injection; a similar trend was observed for serum markers of myocardial injury, apoptosis, and hemodynamic parameters. Compared with the Post group, the Lac+Eda group had similar blood pH values, levels of reactive oxygen species, mitochondrial absorbance, and levels of signal pathway marker. The Lac and Eda groups partly mimicked the protective role. These data suggest that local myocardial administration of lactic acid and low dose of edaravone initiates protective signal pathways of mechanical postconditioning and replicates the myocardial protection.

Excretion of carbon dioxide and L-lactic acid through exhalation and perspiration provides olfactory signals to mosquitoes which allow them to find and bite humans; however, mosquito species differ in this regard. This study investigated upwind responses of Anopheles stephensi, mysorensis form, an important malaria vector in Asia, to carbon dioxide and L-lactic acid under laboratory conditions. While a minimal dose of carbon dioxide (90 ppm) activated the mosquitoes, 10 times this amount suppressed them. L-lactic acid alone did not produce a significant effect by itself, but addition of 6 ug/min of L-lactic acid to a range of 90 to 410 ppm carbon dioxide resulted in attraction. The results provide further support for the hypothesis that CO2 plays an important role in the host-seeking behavior of zoophilic mosquitoes, and suggests that L-lactic acid might play a more critical role than CO2 in the attraction of An. stephensi.

During the pulmonary edema stage ... metabolic acidosis may occur because of increased lactic acid production in response to hypoxemia. /NO2-induced acute lung injury/

Burning and/or stinging is one of the most common concerns expressed by patients using topical therapies for treatment of dermatologic disorders. Topical lactic acid preparations often are used to treat dry scaly skin. In this study, we compared the level of burning/stinging reported by participants with application of lactic acid cream 10% containing strontium versus ammonium lactate lotion 12% and cetearyl alcohol lotion. The mean rating of burning/stinging reported for lactic acid cream 10% with strontium and cetearyl alcohol lotion was lower than ammonium lactate lotion 12% (P<.0001). Based on the study results, lactic acid cream 10% with strontium causes less burning/stinging than ammonium lactate lotion 12%.

For more Interactions (Complete) data for LACTIC ACID (6 total), please visit the HSDB record page.

Health Effects · 1 条

Chronically high levels of Lactic acid are associated with at least a dozen inborn errors of metabolism including: 2-Methyl-3-hydroxybutyryl CoA dehydrogenase deficiency, Biotinidase deficiency, Fructose-1,6-diphosphatase deficiency, Glycogen Storage Disease Type 1A (GSD1A) or Von Gierke Disease, Glycogenosis, Type IB, Glycogenosis, Type IC, Glycogenosis, Type VI. Hers disease, Lactic Acidemia, Leigh Syndrome, Methylmalonate Semialdehyde Dehydrogenase Deficiency, Pyruvate Decarboxylase E1 Component Deficiency, Pyruvate dehydrogenase complex deficiency, Pyruvate dehydrogenase deficiency, Short Chain Acyl CoA Dehydrogenase Deficiency (SCAD Deficiency).

Ecotoxicity Values · 4 条

LC50; Species: Moina micrura (Water Flea) length 0.09 mm and breadth 0.06 mm; Conditions: freshwater, renewal; Concentration: 329120 ug/L for 96 hr (95% confidence interval: 315810-342430 ug/L) /88% purity/

LC50; Species: Oreochromis mossambicus (Mozambique Tilapia) adult, male and female, weight 11.83 g; Conditions: freshwater, renewal; Concentration: 257730 ug/L for 96 hr (95% confidence interval: 210540-315810 ug/L) /88% purity/

LC50; Species: Branchiura sowerbyi (Oligochaete) weight 0.002 g, length 20 mm; Conditions: freshwater, renewal; Concentration: 50820 ug/L for 96 hr (95% confidence interval: 48400-53240 ug/L) /88% purity/

LC50; Species: Oncorhynchus sp (Trout); Concentration: 100 mg/L for 18 hr /Conditions of bioassay not specified in source examined/

Environmental Fate · 3 条

TERRESTRIAL FATE: Based on a classification scheme(1), experimentally-derived Koc values ranging from <0.08 to <20.9(2,3), indicate that lactic acid is expected to have very high mobility in soil(SRC). The pKa of lactic acid is 3.86(4), indicating that this compound will exist partially to almost entirely as an anion in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(5). Volatilization of lactic acid from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 9.6X10-9 atm-cu m/mole(SRC), derived from its vapor pressure, 0.0813 mm Hg(6), and an assigned value for water solubility of 1.0X10+6 mg/L (miscible)(7). Lactic acid is not expected to volatilize from dry soil surfaces(SRC) based upon its vapor pressure(6). A 76% of theoretical BOD using activated sludge in a 2-week Japanese MITI test indicates lactic acid is readily biodegradable(8) and suggests that biodegradation is an important environmental fate process in soil(SRC). Other screening tests have also found lactic acid to biodegrade readily(9-11).

AQUATIC FATE: Based on a classification scheme(1), experimentally-derived Koc values ranging from <0.08 to <20.9(2,3), indicate that lactic acid is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(4) based upon an estimated Henry's Law constant of 9.6X10-9 atm-cu m/mole(SRC), derived from its vapor pressure, 0.0813 mm Hg(5), and an assigned value for water solubility of 1.0X10+6 mg/L (miscible)(6). The pKa of lactic acid is 3.86(7), indicating that this compound will exist partially to almost entirely in the anion form in the environment(SRC). The anion form will not volatilize, but by analogy to the similar acetic acid(8), lactic acid is expected to have a measurable Henry's Law constant even when almost entirely ionized. According to a classification scheme(9), an estimated BCF of 3(SRC), from a log Kow of -0.72(10) and a regression-derived equation(11), suggests the potential for bioconcentration in aquatic organisms is low(SRC). A 76% of theoretical BOD using activated sludge in a 2-week Japanese MITI test indicates lactic acid is readily biodegradable(12) and suggests that biodegradation is an important environmental fate process in water(SRC). Other screening tests have also found lactic acid to biodegrade readily(13-15). Hydrolysis is not expected to be an important environmental fate process since this compound lacks functional groups that hydrolyze under environmental conditions(4).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), lactic acid, which has a vapor pressure of 0.0813 mm Hg at 25 °C(2), is expected to exist solely as a vapor in the ambient atmosphere. Vapor-phase lactic acid 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 2.7 days(SRC), calculated from its rate constant of 5.9X10-12 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Lactic acid does not contain chromophores that absorb at wavelengths >290 nm and therefore is not expected to be susceptible to direct photolysis by sunlight(4).

Food Survey Values · 2 条

Lactic acid was detected as a flavoring constituent of Nigerian gari (a type of tapioca made from cassava (Manihot esculenta) tubers)(1). Lactic acid occurs in sour milk as a result of lactic acid bacteria(2). Lactic acid is also found in molasses due to partial conversion of sugars, in apples and other fruits, tomato juice, beer, wines, opium, ergot, foxglove, and several higher plants, especially during germination(2). Lactic acid is present in many foods both naturally or as a product of in situ microbial fermentation, as in sauerkraut, yogurt, buttermilk, sourdough breads, and many other fermented foods(3).

Lactic acid occurrence in plants(1).[Table#2133]

法规信息

FDA Requirements · 3 条

Substance added directly to human food affirmed as generally recognized as safe (GRAS).

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: lactic acid is included in digestive drug products.

Lactic acid used as a general purpose food additive in animal drugs, feeds, and related products is generally recognized as safe when used in accordance with good manufacturing or feeding practice.

FIFRA Requirements · 5 条

Lactic acid (2-hydroxypropanoic acid) is exempted from the requirement of a tolerance when used as a plant growth regulator in or on all raw agricultural commodities.

Residues of lactic acid are exempted from the requirement of a tolerance when used in accordance with good agricultural practice as inert (or occasionally active) ingredients in pesticide formulations applied to growing crops or to raw agricultural commodities after harvest. Use: solvent.

Residues of lactic acid are exempted from the requirement of a tolerance when used in accordance with good agricultural practice as inert (or occasionally active) ingredients in pesticide formulations applied to animals. Use: solvent.

Residues of the following chemical substances are exempted from the requirement of a tolerance when used in accordance with good manufacturing practice as ingredients in an antimicrobial pesticide formulation, provided that the substance is applied on a semi-permanent or permanent food-contact surface (other than being applied on food packaging) with adequate draining before contact with food. ... (b) The following chemical substances when used as ingredients in an antimicrobial pesticide formulation may be applied to: Dairy processing equipment, and food-processing equipment and utensils. Lactic acid is included on this list. Limit: When ready for use, the end-use concentration is not to exceed 138 ppm.

For more FIFRA Requirements (Complete) data for LACTIC ACID (6 total), please visit the HSDB record page.

化学与工业

药理信息

ATC Code · 3 条

G - Genito urinary system and sex hormones

QP - Antiparasitic products, insecticides and repellents

QG - Genito urinary system and sex hormones

Bionecessity · 3 条

Lactic acidosis is associated with both inherited and acquired metabolic diseases. Lactic acid metabolism in the presence of altered gluconeogenesis, anaerobic glycolysis, and acid-base balance is a major factor in many disorders. Lactic acid can be formed only from pyruvic acid; therefore, disorders that increase pyruvate concentration, enhance lactic acid formation, or reduce lactic acid degradation cause lactic acidosis. Inborn metabolic errors that are accompanied by derangement of metabolic pathways of glucose, pyruvate, amino acids, and organic acids as well as toxic and systemic conditions that promote tissue hypoxia or mitochondrial injury result in lactic acidosis. In the presence of acquired disorders, treatment is directed initially toward modification or cure of the primary condition and then toward eliminating acidosis and other metabolic complications. Specific therapy is available for some inborn errors of metabolism.

Macrophages have an important role in the maintenance of tissue homeostasis. To perform this function, macrophages must have the capacity to monitor the functional states of their 'client cells': namely, the parenchymal cells in the various tissues in which macrophages reside. Tumors exhibit many features of abnormally developed organs, including tissue architecture and cellular composition. Similarly to macrophages in normal tissues and organs, macrophages in tumors (tumor-associated macrophages) perform some key homeostatic functions that allow tumor maintenance and growth. However, the signals involved in communication between tumors and macrophages are poorly defined. Here we show that lactic acid produced by tumor cells, as a by-product of aerobic or anaerobic glycolysis, has a critical function in signalling, through inducing the expression of vascular endothelial growth factor and the M2-like polarization of tumor-associated macrophages. Furthermore, we demonstrate that this effect of lactic acid is mediated by hypoxia-inducible factor 1alpha (HIF1alpha). Finally, we show that the lactate-induced expression of arginase 1 by macrophages has an important role in tumor growth. Collectively, these findings identify a mechanism of communication between macrophages and their client cells, including tumor cells. This communication most probably evolved to promote homeostasis in normal tissues but can also be engaged in tumors to promote their growth.

L-lactic acid is a normal metabolic intermediate produced by most mammalian cells and other organisms, such as bacteria; it is metabolized in preference to D-lactic acid in man, dogs, and rats. Lactic acid is converted to pyruvic acid by lactic acid dehydrogenase.

PharmacodynamicsLactic acid produces a metabolic alkalinizing effect.
Mechanism of ActionLactate ions are metabolized ultimately to carbon dioxide and water, which requires the consumption of hydrogen cations.
Metabolism/Metabolites · 5 条

... Propylene glycol ... is oxidized to lactic acid or pyruvic acid by two pathways. These two metabolites are then used by the body as sources of energy either by oxidation through the tricarboxylic acid cycle or by generation of glycogen through the glycolytic pathway.

Lactic acid diffuses through muscle tissue and is transported to the liver in the bloodstream. In the liver, it is converted to glucose by gluconeogenesis. Lactic acid can also be further catabolized in the lactic acid cycle (also known as the Cori cycle).

L-lactic acid is a normal metabolic intermediate produced by most mammalian cells and other organisms, such as bacteria; it is metabolized in preference to D-lactic acid in man, dogs, and rats. Lactic acid is converted to pyruvic acid by lactic acid dehydrogenase.

In animals, lactate that is generated by anaerobic metabolism can be transported to other more aerobic tissues, such as the liver, where it can be reconverted to pyruvate. The pyruvate can then be further metabolized, reconverted to carbohydrate material as free glucose, or stored as glycogen.

For more Metabolism/Metabolites (Complete) data for LACTIC ACID (8 total), please visit the HSDB record page.

FDA Pharmacological Classification · 6 条

33X04XA5AT

LACTIC ACID, UNSPECIFIED FORM

Mechanisms of Action [MoA] - Acidifying Activity

The mechanism of action of lactic acid, unspecified form is as an Acidifying Activity.

ISHANCARE VAGINAL ANTIBACTERIAL GEL

Acidifying Activity [MoA]

用途与制造

Uses · 6 条

CIR ingredient: Lactic Acid

Used as a solvent and acidulant in the production of foods, drugs, and dyes; Also used as a mordant in woolen goods printing, a soldering flux, a dehairing agent, and a catalyst for phenolic resins; Also used in leather tanning, oil well acidizing, and as a plant growth regulator; [HSDB]

Petroleum Production and Refining [Category: Industry]

The fastest growing use for lactic acid is its use as a monomer for the production of polylactic acid or polylactide (PLA). ... Applications for PLA include containers for the food and beverage industries, films and rigid containers for packaging, and serviceware (cups, plates, utensils). The PLA polymer can also be spun into fibers and used in apparel, fiberfill (pillows, comforters), carpet, and nonwoven applications such as wipes.

It is used in metal plating, cosmetics, and the textile and leather industry.

In dyeing baths, as mordant in printing woolen goods, solvent for water-insoluble dyes (alcohol-soluble induline, nigrosine, spirit-blue). Reducing chromates in mordanting wool. Manufacturing cheese, confectionery. Component of babies' milk formulas; acidulant in beverages; for acidulating worts in brewing. In preparation of sodium lactate injections. Ingredient of cosmetics. Component of spermatocidal jellies. For removing Clostridium butyricum in manufacturing of yeast; dehairing, plumping, and decalcifying hides. Solvent for cellulose formate. Flux for soft solder. Manufacturing lactates which are used in food products, in medicine, and as solvents. Plasticizer, catalyst in the casting of phenolaldehyde resins.

U.S. Exports · 3 条

(1972) No Data

(1975) No Data

(1986) No Data

U.S. Imports · 3 条

(1972) 3.43X10+8 GRAMS

(1973) 6.24X10+8 GRAMS

(1984) 4.96X10+9 g

U.S. Production · 6 条

2023: 100,000,000 - <500,000,000 lb

This chemical is listed as a High Production Volume (HPV) (65FR81686). Chemicals listed as HPV were produced in or imported into the U.S. in >1 million pounds in 1990 and/or 1994. The HPV list is based on the 1990 Inventory Update Rule. (IUR) (40 CFR part 710 subpart B; 51FR21438).

(1975) GREATER THAN 9.1X10+5 GRAMS

(1983) 5.90X10+9 g

(1986) >1 million-10 million pounds

For more U.S. Production (Complete) data for LACTIC ACID (10 total), please visit the HSDB record page.

Consumption Patterns · 2 条

50% used as an acidulant in foods and as an intermediate for emulsifiers for leavened bakery products; 50% in other applications (1973)

85% used for food, beverage & bakery; 10% for textile and leather; and 5% for chemicals & miscellaneous (1982)

Consumer UsesIntermediate

供应商50 家

国药集团化学试剂有限公司86-21-63210123 · [email protected]
郑州阿尔法化工有限公司+86-18530059196 · [email protected]
Shandong chuangyingchemical Co., Ltd.18853181302 · [email protected]
上海康朗生物科技有限公司021-61998208 18217752821 · [email protected]
广州纳珑化工有限公司13192879270; 13192879270 · [email protected]

相关反应

330 条

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