Nonanoic acid ( Pelargonic Acid)

Table of Contents

Nonanoic acid ( Pelargonic Acid)

CAS Number: 112-05-0; Nonanoic acid; Nonoic acid; Nonylic acid; 1-Octanecarboxylic acid; Pelargonic acid; EC Number 203-931-2; chemical formula CH₃(CH₂)₇COOH. Nonanoic acid; n-Nonanoic acid; n-Nonoic acid; n-Nonylic acid; Nonoic acid; Nonylic acid; Pelargic acid; Pelargonic acid; 1-Octanecarboxylic acid; Cirrasol 185a; Emfac 1202; Hexacid C-9; Pelargon; Emery’s L-114; Emery 1202

Pelargonic acid, also called nonanoic acid, is an organic compound with structural formula CH3(CH2)7CO2H. It is a nine-carbon fatty acid. Nonanoic acid is a colorless oily liquid with an unpleasant, rancid odor. It is nearly insoluble in water, but very soluble in organic solvents. The esters and salts of pelargonic acid are called pelargonates or nonanoates.

Pelargonic acid (nonanoic acid) is a monocarboxylic acid. The product appears as a transparent and colourless liquid, and is available in different purity grades.

Pelargonic acid, thanks to its favourable ecotoxicological profile, is used in the formulations of new herbicides, replacing existing synthetic ones.

A C9 straight-chain saturated fatty acid which occurs naturally as esters of the oil of pelargonium. Has antifungal properties, and is also used as a herbicide as well as in the preparation of plasticisers and lacquers.

The non persistence and ultimate biodegradability of natural pelargonic acid herbicides means that their impact on the environment is minimal. They do not interfere with biodiversity and have no residual effects and can be used for soil cleaning even immediately before sowing or transplanting.

Pelargonic acid is also used in cleaning products as a precursor to peroxynonanoic acid.

Peroxycarboxylic acids are known for their antimicrobial activity (sanitisation, disinfection and sterilisation) and as bleaching agents.

Pelargonic acid has thus found a further destination in industrial detergents, water treatments and the control of microbial activity in public spaces.

Some esters of pelargonic acid are used as intermediates in the synthesis of biolubricants and emollients for the cosmetics industry.

Preparation, occurrence, and uses

Pelargonic acid occurs naturally as esters in the oil of pelargonium. Together with azelaic acid, it is produced industrially by ozonolysis of oleic acid.

H17C8CH=CHC7H14CO2H + 4O → HO2CC7H14CO2H + H17C8CO2H

Synthetic esters of pelargonic acid, such as methyl pelargonate, are used as flavorings. Pelargonic acid is also used in the preparation of plasticizers and lacquers. The derivative 4-nonanoylmorpholine is an ingredient in some pepper sprays. The ammonium salt of pelargonic acid, ammonium pelargonate, is an herbicide. It is commonly used in conjunction with glyphosate, a non-selective herbicide, for a quick burn-down effect in the control of weeds in turfgrass.

Pharmacological effects

Pelargonic acid may be more potent than valproic acid in treating seizures. Moreover, in contrast to valproic acid, pelargonic acid exhibited no effect on HDAC inhibition, suggesting that it is unlikely to show HDAC inhibition-related teratogenicity.

NONANOIC ACID

Pelargonic acid

112-05-0

n-Nonanoic acid

Nonoic acid

Nonylic acid

Pelargic acid

n-Nonylic acid

n-Nonoic acid

1-Octanecarboxylic acid

Pelargon

Cirrasol 185A

Hexacid C-9

Emfac 1202

1-nonanoic acid

Fatty acids, C6-12

Fatty acids, C8-10

Pelargon [Russian]

1-Octanecarboxyic acid

Nonansaeure

Pelargonsaeure

pergonic acid

nonoate

NSC 62787

UNII-97SEH7577T

FEMA No. 2784

HSDB 5554EINECS 203-931-2

MFCD00004433

68937-75-7

EPA Pesticide Chemical Code 217500

97SEH7577T

pergonate

n-nonanoate

1-nonanoate

C9:0

octan-1 carboxylic acid

1-octanecarboxylate

n-Nonanoic acid, 97%

67762-36-1

Q-201488CAS-112-05-0

Nonanoicacid

n-Pelargonate

n-Nonylate

Perlargonic acid

n-Nonoate

Nonanoic Acid.

n-pelargonic acid

KNA

EINECS 273-086-2

Nonanoic Acid Anion

Acid C9

Caprylic-Capric Acid

Nonanoic acid, 96%

3sz1

Emery’s L-114

Pelargonic Acid 1202

Emery 1202

Emery 1203

octane-1-carboxylic acid

Nonanoic acid, >=97%

CCCCCCCCC([O])=O

EC 203-931-2

EC 273-086-2

Caprylic-Capric Acid 658

Emery 1202 (Salt/Mix)

4-02-00-01018 (Beilstein Handbook Reference)

Nonanoic acid, >=96%, FG

Nonanoic acid, analytical standard

Nonanoic acid, natural, 98%, FG

Fatty acids C7to C20: Nonanoic acid

Nonanoic acid

Pelargonic Acid

Translated names

acid nonanoic (ro)

Acid nonanoic, acid pelargonic (ro)

acide nonanoique (fr)

Acide nonanoïque, acide pélargonique (fr)

acido nonanoico (it)

Acido nonanoico, acido pelargonico (it)

Aċidu nonanoiku, Aċidu pelargoniku (mt)

kwas nonanowy (pl)

Kwas nonanowy, kwas pelargonowy (pl)

kwas pelargonowy (pl)

Kyselina nonanová, kyselina pelargonová (cs)

kyselina nonánová (sk)

Kyselina nonánová (kyselina pelargónová) (sk)

Nonaanhape (et)

Nonaanhape, pelargoonhape (et)

Nonaanihappo (fi)

Nonaanihappo (pelargonihappo) (fi)

nonaanzuur (nl)

Nonaanzuur, pelar-goonzuur (nl)

nonano rūgštis (lt)

Nonano rūgštis, pelargono rūgštis (lt)

Nonanoic acid, Pelargonic acid (no)

nonanojska kislina (sl)

Nonanojska kislina, pelargonska kislina (sl)

nonanonska kiselina (hr)

nonanová kyselina (cs)

Nonanska kiselina, pelargonična kiselina (hr)

nonansyra (sv)

Nonansyra, pelargonsyra (sv)

nonansyre (da)

Nonansyre og pelargonsyre (da)

Nonansäure (de)

Nonansäure, Pelargonsäure (de)

nonánsav (hu)

Nonánsav, pelargonsav (hu)

Nonānskābe (lv)

ácido nonanoico (es)

Ácido nonanoico, ácido pelargónico (es)

ácido nonanóico (pt)

Ácido nonanóico, Ácido pelargónico (pt)

Εννεανικό οξύ (πελαργονικό οξύ) (el)

εννεανοϊκό οξύ (el)

нонанова киселина (bg)

Нонанова киселина, пеларгонова киселина (bg)

IUPAC names

Acid C9, Pelargonic acid

Pelargonic and realted fatty acids

Trade names

Acido Pelargónico

Prifrac 2913

Prifrac 2914

Prifrac 2915

Synonyms

1-nonanoic acid

1752351 [Beilstein]

267-013-3 [EINECS]

506-25-2 [RN]

Acid C9

Acide nonanoïque [French] [ACD/IUPAC Name]

n-nonanoic acid

n-Nonylic acid

Nonanoic acid [ACD/Index Name] [ACD/IUPAC Name]

Nonansäure [German] [ACD/IUPAC Name]

n-Pelargonic acid

Pelargonic Acid

Pergonic acid

130348-94-6 [RN]

134646-27-8 [RN]

1-OCTANECARBOXYLIC ACID

Cirrasol 185A

EINECS 203-931-2

EINECS 273-086-2

Emery 1203

Emery’S L-114

n-Nonanoic-9,9,9-d3 acid

n-Nonoic acid

Nonansaeure

noncarboxylic acid

nonoic acid

nonylic acid

Pelargic acid

pelargon

Pelargon [Russian]

Pelargon [Russian]

Pelargonic Acid 1202

Pelargonsaeure

Pelargonic Acid does not have any properties that make it more

hazardous than other chemicals used in chemical manufacturing

plants. In general Pelargonic Acid is manufactured in industrial

production plants by trained professionals using a multi-step batch

process. Exposure of worker to the active substance during

manufacturing is very variable and depends strongly on the personal

work hygiene of the individual worker. However, only a small

fraction of the produced Pelargonic Acid is used in biocidal products

marketed in Europe. Fwther main applications of Pelargonic Acid are

lubricant base stocks, textile coning oils, polymerization initiators,

cot1’osion inhibitors, metal cleaners, flotation agents for 1nineral

refining, herbicides, fragrances, PVC plasticizers, cold water bleach

activators and catalyst scavenger.

However, as the active substance Pelargonic Acid is not produced in

the European Union, European monitoring data are not available.

Besides, as the production takes place outside Europe, exposure

assessment during manufacturing of the active substance is not

required. 

Nonanoic acid is a medium-chain saturated fatty acid. It is a volatile compound that has been found in raw and roasted pecans.1 Nonanoic acid inhibits mycelial growth and spore germination in the plant pathogenic fungi M. roreri and C. perniciosa in a concentration-dependent manner.2 It has herbicidal activity against a variety of species, including crabgrass.3,4 Nonanoic acid has been used as an internal standard for the quantification of free fatty acids in olive mill waste waters.5 Formulations containing nonanoic acid have been used in indoor and outdoor weed control and as cleansing and emulsifying agents in cosmetics.

This high purity nonanoic acid is ideal as a standard and for biological studies. Odd numbered fatty acids occur in small amounts in mammals but are found in much larger amounts in bacteria and in some plants (especially in pelargonium) and lower animals. Due to difficulties in their identification the properties and functions of odd numbered fatty acids have not been fully studied, but with better analytical techniques and high purity standards they are now gaining more prevalence in research.1 Odd numbered fatty acids are found in small amounts acylated to various sphingolipids where they have unique properties and functions.2 Microbial fatty acid profiles, which often contain significant amounts of odd numbered fatty acids, are unique from one species to another and can therefore be used in the determination of bacterial identity. Nonanoic acid and its esters are used as herbacides (both as the free acid and as ammonium nonanoate), flavorings, and in the biosynthesizing of polyhydroxyalkenoates. It induces irritancy of the skin but both its mechanism and gene activation are different from other skin irritants.3 Nonanoic acid has been found to be a fungal self inhibitor of Rhizopus oligosporus.4 Sphingolipids are normally acylated with long-chain fatty acids and are critical in many biological functions. When acylated with shorter fatty acids these sphingolipids can more easily cross the cell membrane barrier. Nonanoic acid is a saturated fatty acid and saturated fatty acids have been found to cause moderate risk of coronary heart disease as compared with polyunsaturated fatty acids and they significantly lower the total cholesterol/high density lipoprotein-cholesterol ratio as compared with carbohydrates.

Pelargonic acid is present in many plants. It is used as an herbicide to prevent growth of weeds both

indoors and outdoors, and as a blossom thinner for apple and pear trees. The U.S. Food and Drug

Administration (FDA) has approved this substance for use in food. No risks to humans or the

environment are expected when pesticide products containing pelargonic acid are used according to

the label directions.

I. Description of the Active Ingredient

Pelargonic acid is a chemical substance that is found in almost all species of animals and

plants. Because it contains nine carbon atoms, it is also called nonanoic acid. It is found at

low levels in many of the common foods we eat. It is readily broken down in the

environment.

II. Use Sites, Target Pests, And Application Methods

Pelargonic acid has two distinct uses related to plants: weed killer and blossom thinner.

o Weed killer Growers spray pelargonic acid on food crops and other crops to

protect them against weeds. For food crops, pelargonic acid is allowed to be

applied from planting time until 24 hours before harvest. The pre-harvest

restriction assures that little or no residue remains on the food. The chemical also

controls weeds at sites such as schools, golf courses, walkways, greenhouses, and

various indoor sites.

o Blossom thinner Growers use pelargonic acid to thin blossoms, a procedure that

increases the quality and yield of apples and other fruit trees. Thinning the

blossoms allows the trees to produce fruit every year instead of every other year.

III. Assessing Risks to Human Health

Pelargonic acid occurs naturally in many plants, including food plants, so most people are

regularly exposed to small amounts of this chemical. The use of pelargonic acid as an

herbicide or blossom thinner on food crops is not expected to increase human exposure or

risk. Furthermore, tests indicate that ingesting or inhaling pelargonic acid in small

amounts has no known toxic effects. Pelargonic acid is a skin and eye irritant, and product

labels describe precautions that users should follow to prevent the products from getting

in their eyes or on their skin.

IV. Assessing Risks to the Environment

Pelargonic acid is not expected to have adverse effects on non-target organisms or the

environment. Toxicity tests on non-target organisms, such as birds, fish, and honeybees,

revealed little or no toxicity. The chemical decomposes rapidly in both land and water

environments, so it does not accumulate. Because pelargonic acid is an herbicide, it could

harm non-target plants if pesticide spray drifted beyond the intended target area. Users

are required to minimize drift by using large spray droplets and taking other precautions.

V. Regulatory Information

In 1992, EPA registered (licensed for sale) the first pesticide products containing

pelargonic acid. As of November 1999, four pesticide products registered as weed killers or

blossom thinners contained this active ingredient.

The Food and Drug Administration (FDA) has approved pelargonic acid as a food additive,

and as an ingredient in solutions used commercially to peel fruits and vegetables. These

approvals indicate that FDA considers it safe for humans to eat food containing small

amounts of pelargonic acid. 

In 1995, the Mycogen Corporation introduced Scythe®, a burn-down

herbicide containing 60% of the active ingredient, pelargonic acid. Pelargonic

acid is a naturally occurring, saturated, nine-carbon fatty acid (C9:0). Pelargonic

acid occurs widely in nature in products such as goat’s milk, apples and grapes.

Commercially it is produced by the ozonolysis of oleic acid (C18:1) from beef

tallow.

Pelargonic acid has very low mammalian toxicity (oral, inhalation), is not

mutagenic, teratogenic or sensitizing. It can cause eye and skin irritation and

thus the formulated product carries a WARNING signal word (Category II). It

has a benign environmental profile.

As a herbicide, pelargonic acid causes extremely rapid and non-selective

burn-down of green tissues. The rate of kill is related to temperature, but under

all but the coolest conditions the treated plants begin to exhibit damage within

15-60 minutes and begin to collapse within 1-3 hours of the application.

Pelargonic acid is not systemic and is not translocated through woody tissues.

It is also active against mosses and other cryptograms. Pelargonic acid has no

soil activity. As with most burn-down herbicides, pelargonic acid does not

prevent re-growth from protected buds or basal meristems. Many annual

herbaceous weeds can be killed completely while larger weeds, grasses and

woody plants may re-grow.

There are many practical applications of the rapid burn-down activity of

pelargonic acid. It can be used for spot weeding, edging, lining, turf renewal,

chemical pruning and suckering. It is particularly useful as a directed spray for

killing annual weeds in container-grown woody ornamentals, under greenhouse

benches and in other places where systemic herbicides can cause unwanted

damage. If the spray of pelargonic acid does come in contact with some desired

plants, the damage is strictly limited to those leaves which are actually sprayed.

Pelargonic acid should be applied in at least 75 gallons/acre of total spray

volume as activity declines at lower gallonages. 

Explore: