Pelargonic acid (nonanoic 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 nonanoque, acide plargonique (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 nonanov, kyselina pelargonov (cs)
kyselina nonnov (sk)
Kyselina nonnov (kyselina pelargnov) (sk)
Nonaanhape (et)
Nonaanhape, pelargoonhape (et)
Nonaanihappo (fi)
Nonaanihappo (pelargonihappo) (fi)
nonaanzuur (nl)
Nonaanzuur, pelar-goonzuur (nl)
nonano rūgtis (lt)
Nonano rūgtis, pelargono rūgtis (lt)
Nonanoic acid, Pelargonic acid (no)
nonanojska kislina (sl)
Nonanojska kislina, pelargonska kislina (sl)
nonanonska kiselina (hr)
nonanov kyselina (cs)
Nonanska kiselina, pelargonična kiselina (hr)
nonansyra (sv)
Nonansyra, pelargonsyra (sv)
nonansyre (da)
Nonansyre og pelargonsyre (da)
Nonansure (de)
Nonansure, Pelargonsure (de)
nonnsav (hu)
Nonnsav, pelargonsav (hu)
Nonānskābe (lv)
cido nonanoico (es)
cido nonanoico, cido pelargnico (es)
cido nonanico (pt)
cido nonanico, cido pelargnico (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 Pelargnico
Prifrac 2913
Prifrac 2914
Prifrac 2915
Synonyms
1-nonanoic acid
1752351 [Beilstein]
267-013-3 [EINECS]
506-25-2 [RN]
Acid C9
Acide nonanoque [French] [ACD/IUPAC Name]
n-nonanoic acid
n-Nonylic acid
Nonanoic acid [ACD/Index Name] [ACD/IUPAC Name]
Nonansure [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.