Myristic Acid

HCID 11005CAS 32112-52-0

Basic information

Standard SMILES
CCCCCCCCCCCCCC(=O)O
InChIKey
TUNFSRHWOTWDNC-UHFFFAOYSA-N
Molecular formula
C14H28O2
Average molar mass
228.37 g/mol
Monoisotopic mass
228.20893014

Overview

Tetradecanoic acid is an oily white crystalline solid. (NTP, 1992)

Names & identifiers

Preferred name
Myristic Acid
IUPAC
tetradecanoic acid
English name
Myristic acid
Molecular formula
C14H28O2
Molecular weight
228.37

Names & synonyms

Tetradecanoic acidMYRISTIC ACID544-63-8n-Tetradecanoic acidn-Tetradecoic acidn-Tetradecan-1-oic acidCrodacid1-Tridecanecarboxylic acidHystrene 9014Hydrofol acid 1495Univol U 316SEmery 655
Show more names
FEMA 2764MYRISTATE acidNAA104MyristinsαureMYRISTIC ACID (TETRADECANOIC ACID)14:0
MyristinsaeureMyristic acid, puretetradecoic acidFEMA No. 2764C14:0DTXSID6021666NSC-5028PHILACID-1400

Database identifiers

CAS
32112-52-0、544-63-8
PubChem CID
11005
DTXSID
DTXSID6021666
ChEMBL
CHEMBL111077
ChEBI
CHEBI:28875
UNII
0I3V7S25AW
EC Number
208-875-2、250-924-5
Nikkaji
J4.411C

Properties

Computed structural properties

XLogP
5.3
Topological polar surface area
37.3 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
2
Rotatable bonds
12
Heavy atoms
16

Experimental & physicochemical properties

Chemical ClassesOther Classes -> Organic Acids
DrugsPharmaceuticals -> Listed in ZINC15
Lipids · 2 items

Lipids -> Unambiguous Lipids

Fatty Acyls [FA] -> Fatty Acids and Conjugates [FA01] -> Straight chain fatty acids [FA0101]

Cosmetics · 2 items

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

Cleansing; Emulsifying

SpringerMaterials PropertiesBoiling point
FragrancesFragrance Ingredient (Myristic acid) -> IFRA transparency List

Physicochemical properties

Melting point
52 · 52-54 °C(lit.)
Boiling point
250 °C100 · 250 °C100 mm Hg(lit.)
Density
0.862 · 0.862
vapor pressure
0.01 hPa · <0.01 hPa (20 °C)
FEMA
2764 · 2764 | MYRISTIC ACID
refractive index
60 · nD60 1.4305; nD70 1.4273

Safety & regulation

GHS classification

GHS Classification · 5 items

This chemical does not meet GHS hazard criteria for 80.5% (2188 of 2717) of all reports.

Warning

H319 (13.2%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

P264+P265, P280, P305+P351+P338, and P337+P317 (click each P-code to see the statement)

Aggregated GHS information provided per 2717 reports by companies from 13 notifications to the ECHA C&L Inventory.

Hazard information

Regulatory Information · 4 items

Chemical: Tetradecanoic acid

Tetradecanoic acid is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Tetradecanoic acid 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)

Restricted substance: Lead dimyristate

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

Other Safety InformationIMAP assessments - Tetradecanoic acid: Environment tier I assessment
Fire HazardsThis chemical is probably combustible. (NTP, 1992)
Fire PotentialCombustible
Health HazardsSYMPTOMS: Symptoms of exposure to this compound may include irritation of the skin and eyes.
Hazards SummaryEmergency medical treatment: non-toxic ingestion; [HSDB] May cause skin and eye irritation; [CAMEO] In intravenous, lethal-dose animal studies, causes convulsions; [RTECS]

Safety & protection

Fire FightingFires involving this material can be controlled with a dry chemical, carbon dioxide or Halon extinguisher. (NTP, 1992)
First Aid · 1 item

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

Nonfire Spill Response · 1 item

SMALL SPILLS AND LEAKAGE: Should a spill occur while you are handling this chemical, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with 60-70% ethanol and transfer the dampened material to a suitable container. Use absorbent paper dampened with 60-70% ethanol to pick up any remaining material. Seal the absorbent paper, and any of your clothes, which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 60-70% ethanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.

Disposal Methods · 1 item

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

Protective Action Criteria (PAC) · 3 items

30 [mg/m3]

330 [mg/m3]

2000 [mg/m3]

Personal Protective Equipment (PPE) · 1 item

RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)

Toxicology

Body BurdenThe myristic acid content in milk fat ranges from 15.56 to 22.62% of total acids, with an average myristic acid content of 19.78% of total acids(1).
Interactions · 4 items

CELL GROWTH OF SACCHAROMYCES CEREVISIAE ATCC 12341 WAS INHIBITED BY THE ANTIBIOTIC CERULENIN, A SPECIFIC INHIBITOR OF FATTY ACID & STEROL SYNTHESIS, WAS REVERSED BY MYRISTIC ACID IN A 14:0 RATIO. IT PRODUCED OVER 70% REVERSION OF CELL GROWTH INHIBITION. MYRISTIC ACID TAKEN INTO THE CELLS WAS METABOLIZED & SYNTHESIZED INTO FATTY ACIDS OF A COMPOSITION CLOSELY SIMILAR TO THAT OF THE NATIVE FATTY ACIDS, & THIS WAS CONSIDERED TO BE RESPONSIBLE FOR THE RECOVERY OF CELL GROWTH.

... Reports the results of a 6 week feeding study in rats exposed to a diet that contained 50% fat as caprilic and myristic acids. This resulted in hyperlipidemia but no other effects were reported. ... Describes the results of a 90 day feeding study in rabbits that received 25 mg/kg/day of hydrogenated coconut oil (containing glycerides of lauric, capric, myristic, palmitic, and oleic acids). Rabbits exhibited hypercholesteremia, increased plasma triglycerides and fatty acids, accumulation of cholesterol in the liver and aorta, and alteration of hepatic enzyme activity.

The effect of dietary myristic acid, fed as trimyristin either mixed or interesterified with groundnut oil, on serum cholesterol levels was examined in rats. Incorporation of trimyristin in the oil resulted in marked incr in serum cholesterol levels, compared with rats fed groundnut oil only, although a direct relation between serum cholesterol & the myristic acid content of the dietary fat was not apparent. /Ttrimyristin/

... Associations between serum fatty acid composition as well as fatty acid intakes and prostate cancer risk were examined ... The cohort included 29,133 male smokers aged 50-69 years. During 5-8 years of follow-up, 246 prostate cancer cases were diagnosed. One control was selected and matched by age (1 month) for each case from the cohort subjects alive and free of prostate cancer at the time the case was diagnosed. This study included 198 case-control pairs with baseline serum sample available for both. Fatty acids of serum cholesterol esters were measured as a percentage of total fatty acids, using capillary gas chromatography. Intakes of fatty acids were assessed from a validated self-administered dietary questionnaire ... Twofold risk was found in the highest quartile of serum myristic acid compared with the lowest quartile (odds ratio, 1.93; 95% confidence interval, 1.02-3.64) ...

Ecotoxicity Values · 2 items

LC50 Oryzias latipes (red killifish) 118 mg/L/96 hr; Conditions: semistatic test, renewal every 24 hr. /Sodium salt/

EC50 Methanothrix sp. (bacteria) 4.8 mmol (1096 mg)/L/24 hr; Conditions: upflow anaerobic sludge bed rector (predominant methanogen in sludge: Methanothrix), 30 °C, pH 7, intermittent stirring every 30 min for 30 sec, acetate as carbon source; Effect: inhibition of methanogenic activity (minimum inhibitory concn 2.6 mmol (594 mg)/L/24 hr). /Technical grade/

Environmental Fate · 3 items

TERRESTRIAL FATE: Based on a classification scheme(1), an estimated Koc value of 50,000 for the free acid(SRC), determined from a log Kow of 6.11(2) and a regression-derived equation(3), indicates that undissociated myristic acid is expected to be immobile in soil(SRC). The pKa of myristic acid is 4.90(4), indicating that this compound will exist almost entirely in anion form 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 myristic acid from moist soil surfaces is not expected to be an important fate process(SRC) given the pKa(4). Myristic acid is not expected to volatilize from dry soil surfaces(SRC) based upon a vapor pressure of 1.4X10-6 mm Hg(6). Myristic acid reached 2% of its theoretical BOD over 5 days in a sewage inoculum(7); a half-life of 20 hours was observed for the sodium salt in Warburg tests using an unacclimated sludge inoculum at 25 °C(8).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 50,000 for the free acid(SRC), determined from a log Kow of 6.11(2) and a regression-derived equation(3), indicates that undissociated myristic acid is expected to adsorb to suspended solids and sediment(SRC). A pKa of 4.90(4) indicates myristic acid will exist almost entirely in the anion form at pH values of 5 to 9 and therefore volatilization from water surfaces is not expected to be an important fate process(5). According to a classification scheme(6), an estimated BCF of 56(SRC), from its log Kow(2) and a regression-derived equation(7), suggests the potential for bioconcentration in aquatic organisms is moderate(SRC). Myristic acid reached 2% of its theoretical BOD over 5 days in a sewage inoculum(8); a half-life of 20 hours was observed for the sodium salt in Warburg tests using an unacclimated sludge inoculum at 25 °C(9).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), myristic acid, which has a vapor pressure of 1.4X10-6 mm Hg at 25 °C(2), will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase myristic 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 23 hours(SRC), calculated from its rate constant of 1.7X10-11 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase myristic acid may be removed from the air by wet or dry deposition(SRC). Myristic 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 · 1 item

Myristic acid has been identified as a volatile flavor component of mutton and beef(1). Myristic acid was identified as a volatile constituent of blended nectarine skin and pulp(2). Aerosol emission rates of myristic acid from charbroiling hamburger were 17.1 mg/kg of meat cooked for extra lean hamburger (approx. 10.0% fat) and 87.0 mg/kg of meat cooked for regular hamburger (approx. 21% fat); frying hamburger meat led to a myristic acid emission rate of 6.2 mg/kg of meat cooked(3). Myristic acid was found in paprika oleoresin at <0.1 mg/kg(4).

Milk ConcentrationsENVIRONMENTAL: The myristic acid content in milk fat ranges from 15.56 to 22.62% of total acids, with an average myristic acid content of 19.78% of total acids(1).

Regulatory information

FDA Requirements · 1 item

Myristic acid 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.

Safety data

PPE
dust mask type N95 (US), Eyeshields, Gloves
wgk
-
tsca
TSCA listed
rtecs
QH4375000
hs_code
29159080
Toxicity
LD50 i.v. in mice: 432.6 mg/kg (Or, Wretlind)

Chemistry & industry

Pharmacology

Mechanism of Action · 1 item

... The specific hypothesis tested was that free fatty acid association with CD36, a class B scavenger receptor, induces the activation of endothelial nitric-oxide synthase (eNOS). A human microvascular endothelial cell line and a transfected Chinese hamster ovary cell system were used to determine which free fatty acids stimulate eNOS. Surprisingly, only myristic acid, and to a lesser extent palmitic acid, stimulated eNOS. The stimulation of eNOS was dose- and time-dependent. Competition experiments with other free fatty acids and with a CD36-blocking antibody demonstrated that the effects of myristic acid on eNOS required association with CD36. Further mechanistic studies demonstrated that the effects of myristic acid on eNOS function were not dependent on PI 3-kinase, Akt kinase, or calcium. Pharmacological studies and dominant negative constructs were used to demonstrate that myristic acid/CD36 stimulation of eNOS activity was dependent on the activation of AMP kinase. These data demonstrate an unexpected link among myristic acid, CD36, AMP kinase, and eNOS activity.

Metabolism/Metabolites · 6 items

IN RATS FED COCONUT OIL, MYRISTIC ACID WAS ONE OF THE PRINCIPAL FATTY ACIDS PRESENT IN HEPATIC AND ADIPOSE TISSUE TRIGLYCERIDES. ETHANOL INCR THE PROPORTIONS OF MYRISTIC ACID.

IN ADDITION TO METABOLISM BY BETA-OXIDATION, MYRISTIC ACID HAS BEEN SHOWN TO UNDERGO CHAIN ELONGATION TO PALMITIC & STEARIC ACIDS, DESATURATION TO MYRISTOLEIC ACID & INCORPORATION INTO HEPATIC NEUTRAL LIPIDS (& TO A LESSER EXTENT, PHOSPHOLIPIDS).

THE CONVERSION OF SATURATED FATTY ACIDS TO MONOUNSATURATED FATTY ACIDS BY THE 9000 X G SUPERNATANT RAT LIVER HOMOGENATE WAS LESS FOR MYRISTIC ACID THAN FOR PALMITIC ACID. THESE FATTY ACIDS PRODUCED ONLY DELTA9-MONOENOIC ACIDS OF THE SAME CHAIN LENGTH.

MYRISTATE INCORPORATED FROM (14)C-LABELED ACETATE WAS PREFERENTIALLY ESTERIFIED INTO TRIGLYCERIDE, WHEREAS THE LABELED STEARATE WAS CONVERTED INTO PHOSPHOLIPIDS IN THE ISOLATED RAT ADIPOSE CELLS.

For more Metabolism/Metabolites (Complete) data for MYRISTIC ACID (6 total), please visit the HSDB record page.

Tetradecanoic acid has known human metabolites that include 13-Hydroxytetradecanoic acid.

Absorption, Distribution and Excretion · 3 items

IN NORMAL RATS, HIGHER RADIOACTIVITY WAS FOUND IN HEART, LIVER, SPLEEN & ADRENALS 2 HR AFTER ADMIN OF PALMITIC ACID THAN AFTER ADMIN OF MYRISTIC ACID. IN GRANULOMA POUCH-BEARING RATS, RADIOACTIVITY SHOWED HIGHER DISTRIBUTION IN ADRENALS & POUCH EXUDATE 2 HR AFTER PALMITIC ACID ADMIN, COMPARED TO THOSE GIVEN MYRISTIC ACID. RADIOACTIVITY IN THE POUCH WALL WAS GREATER IN RATS GIVEN MYRISTIC ACID.

Fatty acids originating from adipose tissue stores are either bound to serum albumin or remain unesterified in the blood.

Oleic, Palmitic, Myristic, and Stearic Acids are primarily transported via the lymphatic system, and Lauric Acid is transported by the lymphatic and (as a free fatty acid) portal systems.

Tissue LocationsAdipose Tissue
Cellular LocationsCytoplasm
Metabolite PathwaysFatty Acid Biosynthesis

Uses & manufacturing

Uses · 6 items

CIR ingredient: Myristic Acid

Found in most animal and vegetable fats; [Merck Index] Used as a flavor and fragrance in food, soaps, shaving creams, perfumes, and cosmetics; Also used in lubricants and coatings for anodized aluminum; [HSDB]

Aluminum Producing [Category: Industry]

CHEM INT FOR NITROGEN DERIVS-EG, ALKANOLAMINE CONDENSATES

CHEM INT FOR ISOPROPYL MYRISTATE (EMOLLIENT, PLASTICIZER)

Myristic acid is used in the food industry as a flavor ingredient. It is found widely distributed in fats throughout the plant and animal kingdom, including common human foodstuffs, such as nutmeg.

U.S. Production · 5 items

2023: 10,000,000 - <50,000,000 lb

(1979) 6.95X10+9 G (MIXT WITH C12 ACID)

(1981) 5.54X10+9 G (MIXT WITH C12 ACID)

Production volumes for non-confidential chemicals reported under the Inventory Update Rule. [Table#5500]

Tetradecanoic acid is listed as a High Production Volume (HPV) chemical (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).

Consumer UsesOther
Industry UsesEmulsifier
Methods of Manufacturing · 4 items

Preparation from tall-oil fatty acids: Segessmann, Molnar, U.S. pat 2,481,356 (1949); from 9-ketotetradecanoic acid; by electrolysis of methyl hydrogen adipate + decanoic acid; by Maurer oxidation of myristyl alcohol; from cetanol: Selwitz, U.S. pat. 2,969,380 (1961 to Gulf).

Fractional distillation of coconut acid and other vegetable oils.

Lauric acid, broad cut (fractionation; coproduced with lauric acid, narrow cut).

From fatty acid mixture of palm seed oil.

Formulations/PreparationsGRADES: Technical; 99.8%; FCC
Applications · 5 items

DescriptionMyristic acid, also called tetradecanoic acid , is a common saturated fatty acid with the molecular formula CH3(CH2)12COOH. A myristate is a salt or ester of myristic acid. Myristic acid is named after the nutmeg Myristica fragrans. Nutmeg butter is 75 % trimyristin, the triglyceride of myristic acid. Besides nutmeg, myristic acid is also found in palm kernel oil, coconut oil, butter fat and is a minor component of many other animal fats. It is also found in spermaceti, the crystallized fraction of oil from the sperm whale. Myristic acid is also commonly added co-translationally to the penultimate, nitrogen-terminus, glycine in receptor-associated kinases to confer the membrane localisation of the enzyme. The myristic acid has a sufficiently high hydrophobicity to become incorporated into the fatty acyl core of the phospholipid bilayer of the plasma membrane of the eukaryotic cell. In this way, myristic acid acts as a lipid anchor in biomembranes. The ester isopropyl myristate is used in cosmetic and topical medicinal preparations where good absorption through the skin is desired. Reduction of myristic acid yields myristyl aldehyde and myristyl alcohol.

OccurrenceReported found in nutmeg, palm seed, sperm whale oil, blue cheese, burley tobacco, cooked beef and chicken, fish, rum, apricot, banana, lemon and grapefruit juice, cranberry, guava, grapes, melon, papaya, raspberry, strawberry fruit and jam, cucumber, tomato, many cheeses, thyme, breads, butter, milk, lamb liver, pork, hop oil, beer, cognac, whiskies, peanut oil, cocoa, tea, coconut meat and milk, cloudberry, beans, passion fruit, mushroom, mango, starfruit, tamarind, kelp, cardamom, rice, buckwheat, watercress, malt, wort, loquat, Bourbon vanilla, lemon balm, shrimp, nectarine, crab, scallop, squid, cape gooseberry, Chinese quince, pawpaw and sweet grass oil.

UsesMyristic Acid is a saturated fatty acid obtained from nutmeg,coconut oil and other fats. it has poor water solubility but is soluble in alcohol, chloro- form, and ether. it is used as a lubricant, binder, and defoaming agent.

UsesMyristic acid is a 14-carbon saturated (14:0) fatty acid. In vivo, it is commonly added covalently to the N-terminus of proteins in a co-translational process termed N-myristoylation. In addition, there are examples where N-myristoylation occurs post-translationally, when a hidden myristoylation pattern is exposed.

General DescriptionOily white crystalline solid.

Preparation methods · 2 items

PreparationTo prepare the myristic acid, the methyl ester of the mixed fatty acids or mixed fatty acid methyl ester obtained from the coconut oil or palm kernel oil is subject to vacuum fractionation, obtaining myristic acid. For laboratory preparation, glycerol tris (tetradecanoate) is subject to saponification with 10% sodium hydroxide solution, further being acidified with hydrochloric acid to obtain the free myristic acid. It can also be made from tetradecanol.

PreparationPrepared from the fatty acid mixture of palm seed oil.

Additional notes · 1 item

DefinitionChEBI: Tetradecanoic acid is a straight-chain, fourteen-carbon, long-chain saturated fatty acid mostly found in milk fat. It has a role as a human metabolite, an EC 3.1.1.1 (carboxylesterase) inhibitor, a Daphnia magna metabolite and an algal metabolite. It is a long-chain fatty acid and a straight-chain saturated fatty acid. It is a conjugate acid of a tetradecanoate.

Related reactions

79 records

Linked notes

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