Hypochlorous Acid

Hypochlorous
acid
Hypochlorous acid (ClOH, HClO,

HOCl, or ClHO[2][3]) is a weak acid
that forms when chlorine dissolves
in water, and itself partially
dissociates, forming hypochlorite,
ClO−. HClO and ClO− are oxidizers,
and the primary disinfection agents
of chlorine solutions.[4] HClO
cannot be isolated from these
solutions due to rapid equilibration
with its precursor, chlorine.
Hypochlorous acid
Names
IUPAC name
hypochlorous acid, chloric(I) acid,
chloranol, hydroxidochlorine
Other names
Hydrogen hypochlorite, Chlorine
hydroxide, hypochloric acid
Identifiers
CAS Number 7790-92-3 (https://co

mmonchemistry.cas.
org/detail?cas_rn=77
90-92-3)
3D model (JSmol) Interactive image (htt
ps://chemapps.stola
f.edu/jmol/jmol.php?
model=OCl)
ChEBI CHEBI:24757 (http

s://www.ebi.ac.uk/ch
ebi/searchId.do?che
biId=24757)
ChemSpider 22757 (https://www.

chemspider.com/Ch
emical-Structure.227
57.html)
ECHA InfoCard 100.029.302 (https://

echa.europa.eu/subs
tance-information/-/
substanceinfo/100.0
29.302)
EC Number 232-232-5
PubChem CID 24341 (https://pubch

em.ncbi.nlm.nih.gov/
compound/24341)
UNII 712K4CDC10 (http

s://precision.fda.go
v/uniisearch/srs/uni
i/712K4CDC10)
CompTox Dashboard DTXSID3036737 (htt

(EPA)
ps://comptox.epa.go
v/dashboard/chemic
al/details/DTXSID30
36737)
InChI
InChI=1S/ClHO/c1-2/h2H
Key: QWPPOHNGKGFGJK-UHFFFAOYSA-N
InChI=1/ClHO/c1-2/h2H
Key: QWPPOHNGKGFGJK-UHFFFAOYAT
SMILES
OCl
Properties
Chemical formula HClO
Molar mass 52.46 g/mol
Appearance Colorless aqueous

solution
Density Variable
Solubility in water Soluble
Acidity (pKa) 7.53[1]
Conjugate base Hypochlorite
Hazards
Occupational safety and health

(OHS/OSH):
Main hazards corrosive, oxidizing
agent
NFPA 704 0
3 4
OX
(fire diamond)
Related compounds
Other anions Hypofluorous acid

Hypobromous acid
Hypoiodous acid
Related compounds Chlorine

Calcium hypochlorite
Sodium hypochlorite
Except where otherwise noted, data are

given for materials in their standard
state (at 25 °C [77 °F], 100 kPa).
verify (https://en.wikipedia.org/w/ind
ex.php?title=Special:ComparePages&r
ev1=455335463&page2=Hypochlorous
+acid) (what is ?)
Infobox references
Because of its strong antimicrobial

properties, the related compounds
sodium hypochlorite (NaClO) and
calcium hypochlorite (Ca(ClO)2)
are ingredients in many
commercial bleaches, deodorants,
and disinfectants.[5] The white
blood cells of mammals, such as
humans, also contain
hypochlorous acid as a tool
against foreign bodies.[6] In living
organisms, HOCl is generated by
the reaction of hydrogen peroxide
with chloride ions under the
catalysis of the heme enzyme
myeloperoxidase (MPO).[7]
Like many other disinfectants,

hypochlorous acid solutions will
destroy pathogens, such as COVID-
19, adsorbed on surfaces.[8] In low
concentrations, such solutions can
serve to disinfect open wounds.[9]
History
Hypochlorous acid was discovered
in 1834 by the French chemist
Antoine Jérôme Balard (1802–
1876) by adding, to a flask of
chlorine gas, a dilute suspension of
mercury(II) oxide in water.[10] He
also named the acid and its
compounds.[11]
Despite being relatively easy to

make, it is difficult to maintain a
stable hypochlorous acid solution.
It is not until recent years that
scientists have been able to cost-
effectively produce and maintain
hypochlorous acid water for stable
commercial use.
Uses
In organic synthesis, HClO converts
alkenes to chlorohydrins.[12]
In biology, hypochlorous acid is
generated in activated neutrophils
by myeloperoxidase-mediated
peroxidation of chloride ions, and
contributes to the destruction of
bacteria.[13][14][15]
In medicine, hypochlorous acid

water has been used as a
disinfectant and sanitiser.[6][9][5]
In wound care,[16][17][18] and as of

early 2016 the U.S. Food and Drug
Administration has approved
products whose main active
ingredient is hypochlorous acid for
use in treating wounds and various
infections in humans and pets. It is
also FDA-approved as a
preservative for saline solutions.
In disinfection, it has been used in

the form of liquid spray, wet wipes
and aerosolised application.
Recent studies have shown
hypochlorous acid water to be
suitable for fog and aerosolised
application for disinfection
chambers and suitable for
disinfecting indoor settings such
as offices, hospitals and healthcare
clinics.[19]
In food service and water

distribution, specialized equipment
to generate weak solutions of HClO
from water and salt is sometimes
used to generate adequate
quantities of safe (unstable)
disinfectant to treat food
preparation surfaces and water
supplies.[20][21] It is also commonly
used in restaurants due to its non-
flammable and nontoxic
characteristics.
In water treatment, hypochlorous

acid is the active sanitizer in
hypochlorite-based products (e.g.
used in swimming pools).[22]
Similarly, in ships and yachts,

marine sanitation devices[23] use
electricity to convert seawater into
hypochlorous acid to disinfect
macerated faecal waste before
discharge into the sea.
In deodorization, hypochlorous
acid has been tested to remove up
to 99% of foul odours including
garbage, rotten meat, toilet, stool,
and urine odours.
Formation, stability and

reactions
Addition of chlorine to water gives
both hydrochloric acid (HCl) and
hypochlorous acid (HClO):[24]
Cl2 + H2O ⇌ HClO + HCl

Cl2 + 4 OH− ⇌ 2 ClO− + 2 H2O +
2 e−
Cl2 + 2 e− ⇌ 2 Cl−
When acids are added to aqueous

salts of hypochlorous acid (such
as sodium hypochlorite in
commercial bleach solution), the
resultant reaction is driven to the
left, and chlorine gas is formed.
Thus, the formation of stable
hypochlorite bleaches is facilitated
by dissolving chlorine gas into
basic water solutions, such as
sodium hydroxide.
The acid can also be prepared by

dissolving dichlorine monoxide in
water; under standard aqueous
conditions, anhydrous
hypochlorous acid is currently
impossible to prepare due to the
readily reversible equilibrium
between it and its anhydride:[25]
2 HClO ⇌ Cl2O + H2O K (at 0 °C)

= 3.55 × 10−3 dm3 mol−1
The presence of light or transition

metal oxides of copper, nickel, or
cobalt accelerates the exothermic
decomposition into hydrochloric
acid and oxygen:[25]
2 Cl2 + 2 H2O → 4 HCl + O2

Fundamental reactions
In aqueous solution, hypochlorous

acid partially dissociates into the
anion hypochlorite ClO−:
HClO ⇌ ClO− + H+
Salts of hypochlorous acid are

called hypochlorites. One of the
best-known hypochlorites is NaClO,
the active ingredient in bleach.
HClO is a stronger oxidant than

chlorine under standard
conditions.
2 HClO(aq) + 2 H+ + 2 e− ⇌ Cl2(g) +

2 H2O E = +1.63 V
HClO reacts with HCl to form
chlorine:
HClO + HCl → H2O + Cl2
HClO reacts with ammonia to form

monochloramine:
NH3 + HClO → NH2Cl + H2O
HClO can also react with organic

amines, forming N-chloroamines.
Hypochlorous acid exists in

equilibrium with its anhydride,
dichlorine monoxide.[25]
2 HClO ⇌ Cl2O + H2O K (at

0 °C) = 3.55 × 10−3 dm3 mol−1
Reactivity of HClO with
biomolecules
Hypochlorous acid reacts with a

wide variety of biomolecules,
including DNA, RNA,[15][26][27][28]
fatty acid groups,
cholesterol[29][30][31][32][33][34][35][36]
and proteins.[32][37][38][39][40][41][42]
Reaction with protein sulfhydryl

groups
Knox et al.[40] first noted that HClO

is a sulfhydryl inhibitor that, in
sufficient quantity, could
completely inactivate proteins
containing sulfhydryl groups. This
is because HClO oxidises
sulfhydryl groups, leading to the
formation of disulfide bonds[43]
that can result in crosslinking of
proteins. The HClO mechanism of
sulfhydryl oxidation is similar to
that of monochloramine, and may
only be bacteriostatic, because
once the residual chlorine is
dissipated, some sulfhydryl
function can be restored.[39] One
sulfhydryl-containing amino acid
can scavenge up to four molecules
of HClO.[42] Consistent with this, it
has been proposed that sulfhydryl
groups of sulfur-containing amino
acids can be oxidized a total of
three times by three HClO
molecules, with the fourth reacting
with the α-amino group. The first
reaction yields sulfenic acid (R–
SOH) then sulfinic acid (R–SO2H)
and finally R–SO3H. Sulfenic acids
form disulfides with another
protein sulfhydryl group, causing
cross-linking and aggregation of
proteins. Sulfinic acid and R–SO3H
derivatives are produced only at
high molar excesses of HClO, and
disulfides are formed primarily at
bacteriocidal levels.[28] Disulfide
bonds can also be oxidized by
HClO to sulfinic acid.[43] Because
the oxidation of sulfhydryls and
disulfides evolves hydrochloric
acid,[28] this process results in the
depletion HClO.
Reaction with protein amino

groups
Hypochlorous acid reacts readily

with amino acids that have amino
group side-chains, with the chlorine
from HClO displacing a hydrogen,
resulting in an organic
chloramine.[44] Chlorinated amino
acids rapidly decompose, but
protein chloramines are longer-
lived and retain some oxidative
capacity.[14][42] Thomas et al.[14]
concluded from their results that
most organic chloramines decayed
by internal rearrangement and that
fewer available NH2 groups
promoted attack on the peptide
bond, resulting in cleavage of the
protein. McKenna and Davies[45]
found that 10 mM or greater HClO
is necessary to fragment proteins
in vivo. Consistent with these
results, it was later proposed that
the chloramine undergoes a
molecular rearrangement,
releasing HCl and ammonia to
form an aldehyde.[46] The aldehyde
group can further react with
another amino group to form a
Schiff base, causing cross-linking
and aggregation of proteins.[32]
Reaction with DNA and

nucleotides
Hypochlorous acid reacts slowly

with DNA and RNA as well as all
nucleotides in vitro.[26][47] GMP is
the most reactive because HClO
reacts with both the heterocyclic
NH group and the amino group. In
similar manner, TMP with only a
heterocyclic NH group that is
reactive with HClO is the second-
most reactive. AMP and CMP,
which have only a slowly reactive
amino group, are less reactive with
HClO.[47] UMP has been reported to
be reactive only at a very slow
rate.[15][26] The heterocyclic NH
groups are more reactive than
amino groups, and their secondary
chloramines are able to donate the
chlorine.[28] These reactions likely
interfere with DNA base pairing,
and, consistent with this, Prütz[47]
has reported a decrease in
viscosity of DNA exposed to HClO
similar to that seen with heat
denaturation. The sugar moieties
are nonreactive and the DNA
backbone is not broken.[47] NADH
can react with chlorinated TMP
and UMP as well as HClO. This
reaction can regenerate UMP and
TMP and results in the 5-hydroxy
derivative of NADH. The reaction
with TMP or UMP is slowly
reversible to regenerate HClO. A
second slower reaction that results
in cleavage of the pyridine ring
occurs when excess HClO is
present. NAD+ is inert to HClO.[28][47]
Reaction with lipids
Hypochlorous acid reacts with

unsaturated bonds in lipids, but not
saturated bonds, and the ClO− ion
does not participate in this
reaction. This reaction occurs by
hydrolysis with addition of chlorine
to one of the carbons and a
hydroxyl to the other. The resulting
compound is a chlorohydrin.[29]
The polar chlorine disrupts lipid
bilayers and could increase
permeability.[30] When chlorohydrin
formation occurs in lipid bilayers of
red blood cells, increased
permeability occurs. Disruption
could occur if enough chlorohydrin
is formed.[29][35] The addition of
preformed chlorohydrin to red
blood cells can affect permeability
as well.[31] Cholesterol chlorohydrin
have also been observed,[30][33] but
do not greatly affect permeability,
and it is believed that Cl2 is
responsible for this reaction.[33]
Mode of disinfectant
action
E. coli exposed to hypochlorous
acid lose viability in less than 0.1
seconds due to inactivation of
many vital systems.[24][48][49][50][51]
Hypochlorous acid has a reported
LD50 of 0.0104–0.156 ppm[52] and
2.6 ppm caused 100% growth
inhibition in 5 minutes.[45] However,
the concentration required for
bactericidal activity is also highly
dependent on bacterial
concentration.[40]
Inhibition of glucose oxidation
In 1948, Knox et al.[40] proposed the

idea that inhibition of glucose
oxidation is a major factor in the
bacteriocidal nature of chlorine
solutions. They proposed that the
active agent or agents diffuse
across the cytoplasmic membrane
to inactivate key sulfhydryl-
containing enzymes in the
glycolytic pathway. This group was
also the first to note that chlorine
solutions (HClO) inhibit sulfhydryl
enzymes. Later studies have
shown that, at bacteriocidal levels,
the cytosol components do not
react with HClO.[53] In agreement
with this, McFeters and Camper[54]
found that aldolase, an enzyme
that Knox et al.[40] proposes would
be inactivated, was unaffected by
HClO in vivo. It has been further
shown that loss of sulfhydryls does
not correlate with inactivation.[39]
That leaves the question
concerning what causes inhibition
of glucose oxidation. The discovery
that HClO blocks induction of β-
galactosidase by added lactose[55]
led to a possible answer to this
question. The uptake of
radiolabeled substrates by both
ATP hydrolysis and proton co-
transport may be blocked by
exposure to HClO preceding loss of
viability.[53] From this observation,
it proposed that HClO blocks
uptake of nutrients by inactivating
transport proteins.[38][53][54][56] The
question of loss of glucose
oxidation has been further
explored in terms of loss of
respiration. Venkobachar et al.[57]
found that succinic dehydrogenase
was inhibited in vitro by HClO,
which led to the investigation of
the possibility that disruption of
electron transport could be the
cause of bacterial inactivation.
Albrich et al.[15] subsequently
found that HClO destroys
cytochromes and iron-sulfur
clusters and observed that oxygen
uptake is abolished by HClO and
adenine nucleotides are lost. It was
also observed that irreversible
oxidation of cytochromes
paralleled the loss of respiratory
activity. One way of addressing the
loss of oxygen uptake was by
studying the effects of HClO on
succinate-dependent electron
transport.[58] Rosen et al.[51] found
that levels of reductable
cytochromes in HClO-treated cells
were normal, and these cells were
unable to reduce them. Succinate
dehydrogenase was also inhibited
by HClO, stopping the flow of
electrons to oxygen. Later
studies[49] revealed that Ubiquinol
oxidase activity ceases first, and
the still-active cytochromes reduce
the remaining quinone. The
cytochromes then pass the
electrons to oxygen, which explains
why the cytochromes cannot be
reoxidized, as observed by Rosen
et al.[51] However, this line of
inquiry was ended when Albrich et
al.[37] found that cellular
inactivation precedes loss of
respiration by using a flow mixing
system that allowed evaluation of
viability on much smaller time
scales. This group found that cells
capable of respiring could not
divide after exposure to HClO.
Depletion of adenine
nucleotides
Having eliminated loss of

respiration, Albrich et al.[37]
proposes that the cause of death
may be due to metabolic
dysfunction caused by depletion of
adenine nucleotides. Barrette et
al.[55] studied the loss of adenine
nucleotides by studying the energy
charge of HClO-exposed cells and
found that cells exposed to HClO
were unable to step up their energy
charge after addition of nutrients.
The conclusion was that exposed
cells have lost the ability to
regulate their adenylate pool,
based on the fact that metabolite
uptake was only 45% deficient after
exposure to HClO and the
observation that HClO causes
intracellular ATP hydrolysis. It was
also confirmed that, at
bacteriocidal levels of HClO,
cytosolic components are
unaffected. So it was proposed
that modification of some
membrane-bound protein results in
extensive ATP hydrolysis, and this,
coupled with the cells inability to
remove AMP from the cytosol,
depresses metabolic function. One
protein involved in loss of ability to
regenerate ATP has been found to
be ATP synthetase.[38] Much of this
research on respiration reconfirms
the observation that relevant
bacteriocidal reactions take place
at the cell membrane.[38][55][59]
Inhibition of DNA replication
Recently it has been proposed that

bacterial inactivation by HClO is
the result of inhibition of DNA
replication. When bacteria are
exposed to HClO, there is a
precipitous decline in DNA
synthesis that precedes inhibition
of protein synthesis, and closely
parallels loss of viability.[45][60]
During bacterial genome
replication, the origin of replication
(oriC in E. coli) binds to proteins
that are associated with the cell
membrane, and it was observed
that HClO treatment decreases the
affinity of extracted membranes for
oriC, and this decreased affinity
also parallels loss of viability. A
study by Rosen et al.[61] compared
the rate of HClO inhibition of DNA
replication of plasmids with
different replication origins and
found that certain plasmids
exhibited a delay in the inhibition of
replication when compared to
plasmids containing oriC. Rosen's
group proposed that inactivation of
membrane proteins involved in
DNA replication are the
mechanism of action of HClO.
Protein unfolding and

aggregation
HClO is known to cause post-

translational modifications to
proteins, the notable ones being
cysteine and methionine oxidation.
A recent examination of HClO's
bactericidal role revealed it to be a
potent inducer of protein
aggregation.[62] Hsp33, a
chaperone known to be activated
by oxidative heat stress, protects
bacteria from the effects of HClO
by acting as a holdase, effectively
preventing protein aggregation.
Strains of Escherichia coli and
Vibrio cholerae lacking Hsp33 were
rendered especially sensitive to
HClO. Hsp33 protected many
essential proteins from
aggregation and inactivation due to
HClO, which is a probable mediator
of HClO's bactericidal effects.
Hypochlorites
Hypochlorites are the salts of
hypochlorous acid; commercially
important hypochlorites are
calcium hypochlorite and sodium
hypochlorite.
Production of hypochlorites
using electrolysis
Solutions of hypochlorites can be

produced in-situ by electrolysis of
an aqueous sodium chloride
solution in both batch and flow
processes.[63] The composition of
the resulting solution depends on
the pH at the anode. In acid
conditions the solution produced
will have a high hypochlorous acid
concentration, but will also contain
dissolved gaseous chlorine, which
can be corrosive, at a neutral pH
the solution will be around 75%
hypochlorous acid and 25%
hypochlorite. Some of the chlorine
gas produced will dissolve forming
hypochlorite ions. Hypochlorites
are also produced by the
disproportionation of chlorine gas
in alkaline solutions.
Safety
HClO is classified as Non-
Hazardous by the Environmental
Protection Agency in the US. As
any oxidising agent it can be
corrosive or irritant depending on
its concentration and pH.
In a clinical test, hypochlorous acid

water was tested for eye irritation,
skin irritation, and toxicity. The test
concluded that it was non-toxic
and nonirritating to the eye and
skin.[64]
In a 2017 study, a saline hygiene

solution preserved with pure
hypochlorous acid was shown to
reduce the bacterial load
significantly without altering the
diversity of bacterial species on the
eyelids. After 20 minutes of
treatment, there was >99%
reduction of the Staphylococci
bacteria.[65]
Commercialisation
For disinfection, despite being
discovered a long time ago, the
stability of hypochlorous acid
water is difficult to maintain. In
solution, the active compounds
quickly deteriorate back into salt
water, losing its disinfecting
capability, which makes it difficult
to transport for wide use. Despite
its stronger disinfecting
capabilities, it is less commonly
used as a disinfectant compared to
bleach and alcohol due to cost.
Technological developments have

reduced manufacturing costs and
allow for manufacturing and
bottling of hypochlorous acid water
for home and commercial use.
However, most hypochlorous acid
water has a short shelf life. Storing
away from heat and direct sunlight
can help slow the deterioration.
The further development of
continuous flow electrochemical
cells has been implemented in new
products, allowing the
commercialisation of domestic
and industrial continuous flow
devices for the in-situ generation of
hypochlorous acid for disinfection
purposes.[66]
See also
Dichlorine monoxide: the
corresponding acidic oxide
Hypofluorous acid
Perchloric acid
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04-11). "Hypochlorous Acid as a
Potential Wound Care Agent" (https://w
1853323) . Journal of Burns and
Wounds. 6: e5. ISSN 1554-0766 (https://
www.worldcat.org/issn/1554-0766) .
m.nih.gov/17492050) .
65. Stroman, D. W; Mintun, K; Epstein, A. B;
Brimer, C. M; Patel, C. R; Branch, J. D;
Najafi-Tagol, K (2017). "Reduction in
bacterial load using hypochlorous acid
hygiene solution on ocular skin" (https://
www.ncbi.nlm.nih.gov/pmc/articles/PM
C5402722) . Clinical Ophthalmology. 11:
707–714. doi:10.2147/OPTH.S132851
(https://doi.org/10.2147%2FOPTH.S132
851) . PMC 5402722 (https://www.ncbi.
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External links
National Pollutant Inventory –
Chlorine (https://web.archive.org/
web/20091029202733/http://ww
w.npi.gov.au/database/substance-i
nfo/profiles/20.html)
Reuters – Mystery solved: How

bleach kills germs (https://www.re
uters.com/article/scienceNews/id
USTRE4AC68720081113)
Royal Society of Chemistry-'The

Mole' Magazine, MARCH 2014
issue (http://www.rsc.org/eic/mol
e)
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Hypochlorous Acid

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Hypochlorous

Hypochlorous acid (ClOH, HClO,

CAS Number 7790-92-3 (https://co

ChEBI CHEBI:24757 (http

ChemSpider 22757 (https://www.

ECHA InfoCard 100.029.302 (https://

PubChem CID 24341 (https://pubch

UNII 712K4CDC10 (http

CompTox Dashboard DTXSID3036737 (htt

Chemical formula HClO

Molar mass 52.46 g/mol

Appearance Colorless aqueous

Solubility in water Soluble

Acidity (pKa) 7.53[1]

Conjugate base Hypochlorite

Occupational safety and health

Other anions Hypofluorous acid

Related compounds Chlorine

Except where otherwise noted, data are

Because of its strong antimicrobial

Like many other disinfectants,

Despite being relatively easy to

In medicine, hypochlorous acid

In wound care,[16][17][18] and as of

In disinfection, it has been used in

In food service and water

In water treatment, hypochlorous

Similarly, in ships and yachts,

Formation, stability and

Cl2 + H2O ⇌ HClO + HCl

When acids are added to aqueous

The acid can also be prepared by

2 HClO ⇌ Cl2O + H2O K (at 0 °C)

The presence of light or transition

2 Cl2 + 2 H2O → 4 HCl + O2

In aqueous solution, hypochlorous

Salts of hypochlorous acid are

HClO is a stronger oxidant than

2 HClO(aq) + 2 H+ + 2 e− ⇌ Cl2(g) +

HClO + HCl → H2O + Cl2

HClO reacts with ammonia to form

NH3 + HClO → NH2Cl + H2O

HClO can also react with organic

Hypochlorous acid exists in

2 HClO ⇌ Cl2O + H2O K (at

Hypochlorous acid reacts with a

Reaction with protein sulfhydryl

Knox et al.[40] first noted that HClO

Reaction with protein amino

Hypochlorous acid reacts readily

Reaction with DNA and

Hypochlorous acid reacts slowly

Reaction with lipids

Hypochlorous acid reacts with

In 1948, Knox et al.[40] proposed the

Having eliminated loss of

Inhibition of DNA replication

Recently it has been proposed that