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Myristic Acid

HCID 11005
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Basic information

CAS
32112-52-0
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
Formal charge
0
Complexity
155

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
LogP · 3 items

log Kow = 6.11

6.11

6.11

OdorThe odor should be faint with no rancidity.
Food AdditivesFLAVOR ENHANCER, FLAVORING AGENT OR ADJUVANT, LUBRICANT OR RELEASE AGENT, SURFACE-ACTIVE AGENT -> FDA Substance added to food

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

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]
FDA Requirements

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.

Related reactions

79 records
New reaction record
HRID 25706 reaction equation
HRID 25706As reactantuspto-grants-2005_02
HRID 42720 reaction equation
HRID 42720As reactantuspto-grants-2013_09
HRID 54719 reaction equation
HRID 54719As reactantuspto-grants-1997_04
HRID 54720 reaction equation
HRID 54720As reactantuspto-grants-1997_04
HRID 64715 reaction equation
HRID 64715As reactantuspto-grants-1986_09
HRID 65827 reaction equation
HRID 65827As reactantuspto-grants-1978_12
HRID 198606 reaction equation
HRID 198606As reactantTraining data from https://doi.org/10.1039/C8SC04228D (6/10)
HRID 224467 reaction equation
HRID 224467As reactantuspto-grants-1980_11
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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Density · 3 items

0.8622 at 129 °F (NTP, 1992) - Less dense than water; will float

0.8622 at 54 °C/4 °C

0.8622 @ 54°C

Flavoring AgentsEU Flavoring substances
Viscosity5.83 mPa sec at 70 °C

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
FLAVIS Number
8.016 · 08.016 | Tetradecanoic acid
Flash point
230 °F · >230 °F
storage temp.
room temp
solubility
1.07 mg/l · 1.07mg/l
pka
4.78 · 4.78±0.10(Predicted)
form
Flakes, Powder, Chunks or Crystalline Mass
color
White
Odor
100 % · at 100.00 %. waxy fatty soapy coconut
Odor Type
waxy
biological source
synthetic
Water Solubility
0.1 g/100 · <0.1 g/100 mL at 18 ºC
Specific Heat Capacity
1.89 J/ · Cp(crystal): 1.89 J/(g·K), at 25℃
JECFA Number
113 · 113
Merck
14 · 14,6333
BRN
508624 · 508624
Henry's Law Constant
2 · 2.0×101 mol/(m3Pa) at 25℃, Duchowicz et al. (2020)
Stability
Stable. Incompatible with strong oxidizing agents, bases.
Major Application
flavors and fragrances
Cosmetics Ingredients Functions
SURFACTANT - CLEANSINGPERFUMINGOPACIFYINGFRAGRANCE
Cosmetic Ingredient Review (CIR)
Myristic acid (544-63-8)
InChI
1S/C14H28O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14(15)16/h2-13H2,1H3,(H,15,16)
InChIKey
TUNFSRHWOTWDNC-UHFFFAOYSA-N
SMILES
CCCCCCCCCCCCCC(O)=O
LogP
5.79 · 5.79
CAS DataBase Reference
544 · 544-63-8(CAS DataBase Reference)
Substances Added to Food (formerly EAFUS)
MYRISTIC ACID
EWG's Food Scores
1 · 1
FDA UNII
0 I3V7S25AW · 0I3V7S25AW
NIST Chemistry Reference
Tetradecanoic acid(544-63-8)
EPA Substance Registry System
Myristic acid (544-63-8)
UNSPSC Code
85151701 · 85151701
NACRES
25 · NA.25
Symbol(GHS)
7 · GHS07
Signal word
Warning
Hazard statements
315 · H315-H319-H335
Precautionary statements
261 · P261-P280a-P304+P340-P305+P351+P338-P405-P501a
PPE
95 · dust mask type N95 (US), Eyeshields, Gloves
Hazard Codes
Xi
Risk Statements
36 · 36/37/38-38
Safety Statements
24 · 24/25
WGK Germany
-
RTECS
4375000 · QH4375000
TSCA
TSCA listed
HS Code
29159080 · 29159080
Storage Class
11 · 11 - Combustible Solids
Hazardous Substances Data
544 · 544-63-8(Hazardous Substances Data)
Toxicity
50 i.v · LD50 i.v. in mice: 432.6 mg/kg (Or, Wretlind)
· 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.

Reactive GroupAcids, Carboxylic
Special Reports · 2 items

Cosmetic Ingredient Review; Final Report of the Cosmetic Ingredient Review Expert Panel; Final Report on the Safety Assessment of Oleic Acid, Lauric Acid, Palmitic Acid, Myristic Acid, and Stearic Acid; June 2005.

European Chemicals Bureau; IUCLID Dataset, Myristic acid, pure (CAS #544-63-8) (2000 CD-ROM edition). Available from the Database Query page at: http://ecb.jrc.it/esis/esis.php as of January 24, 2008.

EPA Safer ChemicalChemical: Tetradecanoic acid
Reactivity Profile · 1 item

TETRADECANOIC ACID is a carboxylic acid. Carboxylic acids donate hydrogen ions if a base is present to accept them. They react in this way with all bases, both organic (for example, the amines) and inorganic. Their reactions with bases, called "neutralizations", are accompanied by the evolution of substantial amounts of heat. Neutralization between an acid and a base produces water plus a salt. Carboxylic acids with six or fewer carbon atoms are freely or moderately soluble in water; those with more than six carbons are slightly soluble in water. Soluble carboxylic acid dissociate to an extent in water to yield hydrogen ions. The pH of solutions of carboxylic acids is therefore less than 7.0. Many insoluble carboxylic acids react rapidly with aqueous solutions containing a chemical base and dissolve as the neutralization generates a soluble salt. Carboxylic acids in aqueous solution and liquid or molten carboxylic acids can react with active metals to form gaseous hydrogen and a metal salt. Such reactions occur in principle for solid carboxylic acids as well, but are slow if the solid acid remains dry. Even "insoluble" carboxylic acids may absorb enough water from the air and dissolve sufficiently in it to corrode or dissolve iron, steel, and aluminum parts and containers. Carboxylic acids, like other acids, react with cyanide salts to generate gaseous hydrogen cyanide. The reaction is slower for dry, solid carboxylic acids. Insoluble carboxylic acids react with solutions of cyanides to cause the release of gaseous hydrogen cyanide. Flammable and/or toxic gases and heat are generated by the reaction of carboxylic acids with diazo compounds, dithiocarbamates, isocyanates, mercaptans, nitrides, and sulfides. Carboxylic acids, especially in aqueous solution, also react with sulfites, nitrites, thiosulfates (to give H2S and SO3), dithionites (SO2), to generate flammable and/or toxic gases and heat. Their reaction with carbonates and bicarbonates generates a harmless gas (carbon dioxide) but still heat. Like other organic compounds, carboxylic acids can be oxidized by strong oxidizing agents and reduced by strong reducing agents. These reactions generate heat. A wide variety of products is possible. Like other acids, carboxylic acids may initiate polymerization reactions; like other acids, they often catalyze (increase the rate of) chemical reactions.

Air and Water ReactionsInsoluble in water.

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).
Toxicity Summary · 3 items

The CIR Expert Panel concluded that the following ingredients are safe in the present practices of use andconcentration described in the safety assessment when formulated to be non-irritating and non-sensitizing, which may be basedon a QRA...Myristic Acid...

Safe for use in cosmetics, with qualifications

The existing information was reviewed by the independent Expert Panel for Fragrance Safety and supports the use of Myristic acid as described in this fragrance ingredient safety assessment. Data for myristic acid and from read-across analog palmitic acid show that Myristic acid is not expected to be genotoxic. The repeated dose toxicity, reproductive toxicity, and local respiratory toxicity endpoints were evaluated using the Threshold of Toxicological Concern (TTC) for a Cramer Class I material, and the exposures are below the TTC for these endpoints. Data for myristic acid and for read-across analog nonionic acid show that there are no safety concerns for skin sensitization under the current declared levels of use. Myristic acid is not expected to be photoirritating/photoallergenic based on evaluation of the ultraviolet/visible (UV/Vis) spectra.

Average Daily Intake · 2 items

Fatty acids are an important part of the normal daily diet of mammals, birds and invertebrates.

Annual consumption is 1400.00 lb. Individual consumption is 0.001186 mg/kg/day.

Ecotoxicity Excerpts · 5 items

/AQUATIC SPECIES/ A non-photosynthetic mutant of /Euglena gracilis (algae)/ strain Z was used /in/ determination of growth /(biomass)/ at ... /5 g/L of myristic acid with/ continuous shaking /at/ 27 °C, pH 3.3. Test substance floated on surface in initial phase of growth, but insol material was consumed during growth. Previous adaptation was required for growth. Stationary phase was reached after 5 days.

/AQUATIC SPECIES/ No mortality /of Hyale plumulosa (gammarus)/ occured at saturation /of myristic acid/ at 25 + / - 2 °C, pH 8.2, salinity 25 ppt for 48 hr in a saltwater test.

/OTHER TERRESTRIAL SPECIES/ Beauveria bassiana (fungus) was incubated in complex medium at 25 °C for 24 hr with 500 mg/L myristic acid (acetone as solvent). After the addition of test substances pH was adjusted to 6.0 with NaOH. Germination of conidia were 75% for myristic acid and 71% for acetone control.

/OTHER TERRESTRIAL SPECIES/ Paecilomyces fumoso-roseus (fungus) was incubated in complex medium at 25 °C for 24 hr with 500 mg/L myristic acid (acetone as solvent). After the addition of test substances pH was adjusted to 6.0 with NaOH. Germination of conidia were 50% for myristic acid and 71% for acetone control.

/OTHER TERRESTRIAL SPECIES/ Myristic acid was included at a final concn of 2.5% (25 g/L) in a diet containing amino acids, vitamins and glucose and fed to /Pseudosarcophaga affinis (not soil dwelling arthropod)/ larvae at 23 °C. There were 1.7% mortality after 24 hr and 3.1% after 7 days. /Potassium salt/

Plant Concentrations · 1 item

Myristic acid was found in fine particulate matter released (by resuspension and agitation of the leaf composites) from green and dead plant leaves, from plant species characteristic of the Los Angeles area, at concns of 147.8 and 237.4 ug/g, respectively(1). Myristic acid was identified as a volatile constituent of blended nectarine skin and pulp(2). Myristic acid was found in paprika oleoresin at <0.1 mg/kg(3).

Animal ConcentrationsMyristic acid occurs in most animal fats; it has been found in considerable amounts (up to 15%) in sperm whale oil(1).
Effluent Concentrations · 5 items

Myristic acid was detected in aqueous industrial effluent extracts collected between Nov 1979-81 in the following industrial categories (concn in one effluent extract): paint and ink (17 ng/uL); printing and publishing (23 ng/uL); textile mills (4 ng/uL); electronics (5513 ng/uL); amusements and athletic goods (470 ng/uL); and publicly owned treatment works at an unknown concn(1). Myristic acid was identified in the effluent of two publicly owned treatment works (POTW) facilities located in an industrial area of NJ and a rural area of NJ at estimated concns of 5 and 69 ppb, respectively(2). Grab samples of the final effluent from the Addison and Decatur, IL POTWs, obtained in April and June 1980, respectively, were found to contain myristic acid at unreported concns(3). A sample of final effluent, 50% grab and 50% 8 hour composite, obtained from the St. Charles, IL POTW in March 1980, was found to contain myristic acid at an unreported concn(3). Myristic acid was detected in the bleaching effluent from straw pulping and in the combined mill effluent from a straw pulp mill in Denmark at unreported concns(4). Myristic acid was detected in Los Angeles County wastewater treatment plant effluent, collected between Nov 1980 and Aug 1981, at a concn of 1200 ug/L(5). Myristic acid was identified in vapor at concns of 100 to 300 ng/cu m and on particles at concns of 8 to 600 ng/g emitted during combustion of coal at the Ames power plant in Iowa(6). Wastewater from two kraft paper mills in Georgia sampled in March 1972 were found to contain approximately 0.010 and 0.020 mg/L myristic acid (identified as the methyl derivative)(7). An effluent-irrigated citrus grove near Glil-Yam, Israel was found to contain 15 ppb myristic acid at a depth of 20 m in the unsaturated soil zone(8). Myristic acid was identified in the acidic fraction of 5 to 7 day sewage and sludge composites from the Iona Island Sewage Treatment Plant, British Columbia at concns ranging from 23 to 150 ug/L(9). Myristic acid was found at a maximum concn of 109 ng/L in groundwater contaminated by industrial wastes near Barcelona, Spain(10). The mean myristic acid concn in discharged effluent waters (24 hour composite samples) from a pulp mill producing 75,000 tons of pulp annually near Kawerau, New Zealand, in Nov to Dec 1991 and Jan to Feb 1992, was 41 ppb(11). Myristic acid was detected in two effluent samples taken from a sewage treatment plant in Prestwich, North West England, at a mean concn of 4.05 ug/L(12). Myristic acid has been identified in leachate samples collected from the interior of a municipal landfill situated in Gryta, Vasteras, Sweden in May 1990, concn unknown(13).

Fine particle aerosol emission rates of myristic acid from heavy-duty diesel trucks, noncatalyst-equipped, and catalyst-equipped automobiles were 45.7, 1.7, and 11.9 ug/km, respectively(1). Myristic acid was detected in road dust particles collected from paved streets in a residential area of Pasadena, CA in May 1988 at a concn of 171.8 ug/g of particle sample; brake lining particles at a concn of 8.1 ug/g of particle sample; and tire wear particles at a concn of 634.5 ug/g of particle sample(2). Myristic acid was emitted from medium duty diesel trucks at 5.3 ug/km(3).

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)
risk_code
36/37/38-38
Signal word
Warning
Symbol(GHS)
GHS07
hazard_code
Xi
safety_code
24/25
Storage Class
11 - Combustible Solids
Hazard statements
H315-H319-H335
Precautionary statements
P261-P280a-P304+P340-P305+P351+P338-P405-P501a
Hazardous Substances Data
544-63-8(Hazardous Substances Data)

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
Household ProductsInformation on 40 consumer products that contain Myristic acid in the following categories is provided:
Use Classification · 6 items

EPA Safer Chemical Functional Use Classes -> Surfactants

Safer Chemical Classes -> Green circle - The chemical has been verified to be of low concern

Fragrance Ingredients

Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes

Flavoring Agents -> JECFA Flavorings Index

Cosmetics -> Cleansing; Emulsifying

General Manufacturing Information · 4 items

Not Known or Reasonably Ascertainable

Tetradecanoic acid: ACTIVE

Potassium salts of fatty acids are used as insecticides, acaricides, herbicides and algaecides. They are used to control a variety of insects and mosses, algae, lichens, liverworts and other weeds, in or on many food and feed crops, ornamental flower beds, house plants, trees, shrubs, walks and driveways, and on dogs, puppies and cats. /Fatty acid salts/

Commercial products contain 91 to 93% C14 or 96 to 99% C14.

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.

Upstream & downstream products

Upstream raw materials

PALM KERNEL OIL7-Ethyl-2-methyl-4-undecanolFatty acid mixtureMetaclazepamCoconut oilammonium myristate14-Octacosanone, 15-hydroxy-1,2-Dimyristoyl-sn-glycero-3-phosphoethanolamine1-Pentadecene6-Bromohexanoic acid1-Bromooctane

Downstream products

Orris oilMethyl myristateEthoxylatedmono-anddi-glyceridesalkoxy ethanolamido sulfosuccinate sodium saltEthyl myristate1-TetradecanolTetradecanalIsopropyl myristatePalmitoleic acidPalmityl myristateN-Tetradecanamide
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.

Fine particle emission rates for myristic acid from a natural gas-fired water heater and a natural gas-fired space heater were determined(1). A HEPA-filtered dilution air sample emission rate for myristic acid was determined to be 3.7 pg/kJ; the emission rate for myristic acid through the first filter was determined to be 59.6 pg/kJ; the emission rate for myristic acid through the backup filter was 29.9 pg/kJ(1). Myristic acid was found in candle smoke from paraffin and beeswax at 0.61 and 0.59 mg/g of organic compounds(2). Myristic acid was found in wood smoke from red maple(3), red oak(3), paper birch(3), white pine(3), hemlock(3), balsam fir(3), yellow poplar(4), white ash(4), sweet gum(4), mockernut hickory(4), loblolly pine(4), and slash pine(4). Myristic acid was detected in wood smoke from pine, oak and synthetic logs at 1.74, 4.89 and 2.27 mg/kg of wood burnt(5). Myristic acid was found at 0.764, 1.36 and 1.12 mg/kg of burnt pine, oak and eucalyptus wood, respectively, in the particulate phase and at 0.357 mg/kg of burnt pine in the gas phase(6). Myristic acid was found in extract from a pine wood burning campfire at 170 ng/g(7). Myristic acid was found in the fine aerosols from boilers burning number 2 distillate fuel oil at a rate of 879.8 pg/kJ (burning at 58% capacity with 6.5% excess oxygen in stack gases) and a rate of 283.8 pg/kJ (burning at 54% capacity with 7.1% excess oxygen in stack gases)(8). Myristic acid was found at 894.9 ug/g from heated roofing tar pot fumes(9). Myristic acid was found at 4040 and 17,700 ug/kg in the gas and particulate matter from charbroiling meat(10). Myristic acid was detected in the smoke from charring/burning of chitin biopolymers(11).

IN THE FATS EXTRACTED FROM TANNERY & MUNICIPAL SLUDGE, MYRISTIC ACID WAS ONE OF THE MINOR COMPONENTS IDENTIFIED.

MYRISTIC ACID WAS IDENTIFIED IN THE SLUDGE EXTRACTIONS FROM POINT EDWARD PLANT IN CANADA. THE SLUDGE INHIBITED GROWTH OF ORCHARD GRASS IN LAND DISPOSAL.