N-Butyl lactate

Last updated
n-Butyl lactate
Butyl lactate.svg
Names
Preferred IUPAC name
Butyl 2-hydroxypropanoate
Other names
Butyl ester of 2-hydroxypropanoic acid
Butyl ester of lactic acid
Butyl 2-hydroxypropanoate
Butyl α-hydroxypropionate
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.004.834 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 205-316-4
MeSH C114966
PubChem CID
RTECS number
  • OD4025000
UNII
  • InChI=1S/C7H14O3/c1-3-4-5-10-7(9)6(2)8/h6,8H,3-5H2,1-2H3
    Key: MRABAEUHTLLEML-UHFFFAOYSA-N
  • CCCCOC(=O)C(C)O
Properties
C7H14O3
Molar mass 146.186 g·mol−1
AppearanceClear, colorless to white liquid
Odor Mild, transient
Density 0.98 g/cm3 (20°C) [1]
Melting point −43 °C; −45 °F; 230 K [1]
Boiling point 188 °C; 370 °F; 461 K [1]
slightly soluble [1]
Solubility Soluble in ethyl ether, ethanol [2]
Vapor pressure 0.4 mmHg (20°C) [1]
Hazards
Flash point 71 °C; 160 °F; 344 K [1]
382 °C (720 °F; 655 K) [2]
Lethal dose or concentration (LD, LC):
>5 g/kg (oral, rabbit) [3]

>2000 mg/kg (oral, rat) [3]
>5 g/kg (skin, rabbit) [3]
>5000 mg/kg (skin, rat) [3]
12 g/kg (subcutaneous, rat) [3]

Contents

11 g/kg (subcutaneous, mouse) [3]
NIOSH (US health exposure limits):
REL (Recommended)
5 ppm (25 mg/m3) [1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

n-Butyl lactate is an industrial chemical and food additive.

Uses

In an industrial context, n-butyl lactate is used as a solvent and as a chemical feedstock. It is used as a dairy-related flavoring agent. [2]

Metabolism

It is metabolized to lactic acid, which is in turn metabolized to n-butanol, n-butyraldehyde, and n-butyric acid. [4]

Safety

n-Butyl lactate reacts with strong acids, strong bases, and oxidizers. It is also flammable. Exposure to dangerous amounts can occur through inhalation, ingestion, skin contact, or eye contact and causes irritation of the affected area, drowsiness, headache, central nervous system depression, nausea, and vomiting. [1] It is approved as a food additive by the US Food and Drug Administration. [4]

Related Research Articles

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<span class="mw-page-title-main">Lactic acid</span> Group of stereoisomers

Lactic acid is an organic acid. It has the molecular formula CH3CH(OH)COOH. It is white in the solid state and it is miscible with water. When in the dissolved state, it forms a colorless solution. Production includes both artificial synthesis as well as natural sources. Lactic acid is an alpha-hydroxy acid (AHA) due to the presence of a hydroxyl group adjacent to the carboxyl group. It is used as a synthetic intermediate in many organic synthesis industries and in various biochemical industries. The conjugate base of lactic acid is called lactate. The name of the derived acyl group is lactoyl.

<span class="mw-page-title-main">Phosphoric acid</span> Chemical compound (PO(OH)3)

Phosphoric acid is a colorless, odorless phosphorus-containing solid, and inorganic compound with the chemical formula H3PO4. It is commonly encountered as an 85% aqueous solution, which is a colourless, odourless, and non-volatile syrupy liquid. It is a major industrial chemical, being a component of many fertilizers.

<span class="mw-page-title-main">Diisopropyl ether</span> Chemical compound

Diisopropyl ether is a secondary ether that is used as a solvent. It is a colorless liquid that is slightly soluble in water, but miscible with organic solvents. It is used as an extractant and an oxygenate gasoline additive. It is obtained industrially as a byproduct in the production of isopropanol by hydration of propylene. Diisopropyl ether is sometimes represented by the abbreviation DIPE.

<span class="mw-page-title-main">2-Butanol</span> Secondary alcohol

Butan-2-ol, or sec-butanol, is an organic compound with formula CH3CH(OH)CH2CH3. Its structural isomers are 1-butanol, isobutanol, and tert-butanol. 2-Butanol is chiral and thus can be obtained as either of two stereoisomers designated as (R)-(−)-butan-2-ol and (S)-(+)-butan-2-ol. It is normally encountered as a 1:1 mixture of the two stereoisomers — a racemic mixture.

<i>tert</i>-Butyl alcohol Chemical compound

tert-Butyl alcohol is the simplest tertiary alcohol, with a formula of (CH3)3COH (sometimes represented as t-BuOH). Its isomers are 1-butanol, isobutanol, and butan-2-ol. tert-Butyl alcohol is a colorless solid, which melts near room temperature and has a camphor-like odor. It is miscible with water, ethanol and diethyl ether.

<span class="mw-page-title-main">2-Butoxyethanol</span> Chemical compound

2-Butoxyethanol is an organic compound with the chemical formula BuOC2H4OH (Bu = CH3CH2CH2CH2). This colorless liquid has a sweet, ether-like odor, as it derives from the family of glycol ethers, and is a butyl ether of ethylene glycol. As a relatively nonvolatile, inexpensive solvent, it is used in many domestic and industrial products because of its properties as a surfactant. It is a known respiratory irritant and can be acutely toxic, but animal studies did not find it to be mutagenic, and no studies suggest it is a human carcinogen. A study of 13 classroom air contaminants conducted in Portugal reported a statistically significant association with increased rates of nasal obstruction and a positive association below the level of statistical significance with a higher risk of obese asthma and increased child BMI.

<span class="mw-page-title-main">Calcium lactate</span> Chemical compound

Calcium lactate is a white crystalline salt with formula C
6
H
10
CaO
6
, consisting of two lactate anions H
3
C
(CHOH)CO
2
for each calcium cation Ca2+
. It forms several hydrates, the most common being the pentahydrate C
6
H
10
CaO
6
·5H
2
O
.

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n-Butyl acetate is an organic compound with the formula CH3CO2(CH2)3CH3. A colorless, flammable liquid, it is the ester derived from n-butanol and acetic acid. It is found in many types of fruit, where it imparts characteristic flavors and has a sweet smell of banana or apple. It is used as an industrial solvent.

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The chemical compound isobutyl acetate, also known as 2-methylpropyl ethanoate or β-methylpropyl acetate, is a common solvent. It is produced from the esterification of isobutanol with acetic acid. It is used as a solvent for lacquer and nitrocellulose. Like many esters it has a fruity or floral smell at low concentrations and occurs naturally in raspberries, pears and other plants. At higher concentrations the odor can be unpleasant and may cause symptoms of central nervous system depression such as nausea, dizziness and headache.

<span class="mw-page-title-main">Propyl acetate</span> Chemical compound

Propyl acetate, also known as propyl ethanoate, is an organic compound. Nearly 20,000 tons are produced annually for use as a solvent. This colorless liquid is known by its characteristic odor of pears. Due to this fact, it is commonly used in fragrances and as a flavor additive. It is formed by the esterification of acetic acid and propan-1-ol, often via Fischer–Speier esterification, with sulfuric acid as a catalyst and water produced as a byproduct.

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Benzyl butyl phthalate (BBP) is an organic compound historically used a plasticizer, but which has now been largely phased out due to health concerns. It is a phthalate ester of containing benzyl alcohol, and n-butanol tail groups. Like most phthalates, BBP is non-volatile and remains liquid over a wide range of temperatures. It was mostly used as a plasticizer for PVC, but was also a common plasticizer for PVCA and PVB.

<i>tert</i>-Butyl acetate Chemical compound

tert-Butyl acetate, t-butyl acetate or TBAc is a colorless flammable liquid with a camphor- or blueberry-like smell. It is used as a solvent in the production of lacquers, enamels, inks, adhesives, thinners and industrial cleaners. It has recently gained EPA volatile organic compound (VOC) exempt status.

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References

  1. 1 2 3 4 5 6 7 8 NIOSH Pocket Guide to Chemical Hazards. "#0082". National Institute for Occupational Safety and Health (NIOSH).
  2. 1 2 3 CID 8738 from PubChem
  3. 1 2 3 4 5 6 "N-butyl lactate". CDC/NIOSH. 28 March 2018.
  4. 1 2 "n-Butyl lactate". OSHA.