IPBC (IODOPROPYNYL BUTYLCARBAMATE)

Synonyms:
IPBC; 55406-53-6; Iodopropynyl butylcarbamate; 3-iodoprop-2-yn-1-yl butylcarbamate; Iodocarb; Ipbc; 3-Iodo-2-propynyl butylcarbamate; Woodlife; 1-Iodoprop-1-yn-3-yl N-n-butylcarbamate; Carbamic acid, butyl-, 3-iodo-2-propynyl ester; Troysan KK-108A; Troysan polyphase anti-mildew; Caswell No. 501A; 3-iodoprop-2-ynyl N-butylcarbamate; UNII-603P14DHEB; HSDB 7314; Butyl-3-iodo-2-propynylcarbamate; 3-Iodo-2-propynyl butyl carbamate; 3-Iodo-2-propynyl-N-butylcarbamate; EINECS 259-627-5; EPA Pesticide Chemical Code 107801; BRN 2248232; 603P14DHEB; CHEBI:83279; 3-iodoprop-2-ynyl butylcarbamate; Carbamic acid, N-butyl-, 3-iodo-2-propyn-1-yl ester; DSSTox_CID_8038; Carbamic acid, butyl-3-iodo-2-propynyl ester; 3-Iodo-2-propynyl N-butylcarbamate, 97%; 3-IODO-2-PROPYNYL BUTYL CARBBAMATE; 3-Iodoprop-2-yn-1-yl butylcarbamate 55406-53-6; Iodo propynyl butyl carbamate; İodopropynyl butylcarbamate; İodo propynyl butylcarbamate; İPBC

IPBC (Iodopropynyl butylcarbamate)

Iodopropynyl butylcarbamate
Iodopropynyl Butyl Carbamate (IPBC) is a water-soluble preservative used globally in the paints & coatings, wood preservatives, personal care, and cosmetics industries. IPBC is a member of the carbamate family of biocides.[1] IPBC was invented in the 1970s and has a long history of effective use as an antifungal technology.

History
IPBC was initially developed for use in the paint & coatings industry as a dry-film preservative to protect interior and exterior coatings from mold, mildew, and fungal growth, while also offering cost performance and sustainability benefits. IPBC exhibits efficacy against a broad spectrum of fungal species, typically at very low use levels. IPBC today is incorporated into a wide variety of interior and exterior paint formulations around the world.

Use is restricted in some countries due to its toxicity, especially acute inhalation toxicity. IPBC is also becoming recognized as a contact allergen.[2]

Uses
IPBC is an effective fungicide at very low concentrations in cosmetic and other products, and has shown very low sensitivity in humans tested with this preservative. IPBC was approved in 1996 for use up to 0.1% concentrations in topical products and cosmetics. However, this preservative is mostly found in cosmetics at about one-eighth that level [Maier et al., 2009]. IPBC Toxicity and Safety Tests show it to be generally safe: When used properly in leave-on skin products, IPBC is extremely safe [Steinberg, 2002]. Previous to being approved for cosmetic use in 1996, extensive safety and toxicity tests were conducted on IPBC and their results were gathered along with earlier studies in a report of the Safety Assessment of IPBC by the Cosmetic Ingredient Review [CIR Final Report, Lanigan 1998]. This final report found IPBC to be a non-carcinogen with no genotoxicity and in reproductive and developmental toxicity studies using rats and mice, IPBC had no significant effect on fertility, reproductive performance, or on the incidence of fetal malformation [Lanigan, 1998].

Toxicity
The study, "Final Report on the Safety Assessment of Iodopropynyl Butylcarbamate", discusses the results of 32 studies between 1990 and 1994 in 3,582 subjects using skin application of IPBC at relevant concentrations. [3] All 32 studies showed no evidence of contact sensitization compared to placebo controls, with the report stating "With each test formulation, a few panelists had erythema, edema, and/or a papular response, but overall, the results were negative." In addition, the study mentions two skin sensitivity studies on 183 children ages 3 – 12 yrs which showed no adverse effects as well as no significant irritation from IPBC.

Since the early safety report, there have been a few reports of human skin sensitivity to IPBC in individual patients – all of which showed complete recovery after discontinuance of use of any product containing the IPBC which was presumably an allergen for these patients [Toholka & Nixon, 2014; Pazzaglia & Tosti, 1999].

Post-1996 tests of human sensitivity to IPBC have all shown quite low sensitivity, having overall reported human skin testing (patch test) on 53,774 subjects with only 491 of those subjects showing any reaction (0.8%) to IPBC. In every study, positive patch test reactions occurred in less than 1% of subjects tested in all but one study. This is a very low reaction rate, but it is not zero, and the industry reports this low rate of reaction even though in the largest study of 25,435 subjects over 69% of the reactions were either weak or doubtful [Warshaw et al., 2013a].

These combined studies showing prevalence of reaction below 1% means that IPBC at this time does not have the reaction rates necessary to be included as an allergen in standard allergy series. But, it remains under close monitoring as it is a relatively new preservative for cosmetic products and will presumably increase in usage [Sasseville, 2004].

Most human patch tests performed before 2004 were with 0.1% IPBC solutions, i.e. 10 times the concentration used in many cosmetic products. Some used 0.5% IPBC. In 2004, it was suggested that a better concentration for tests of this substance would be 0.2% [Brasch et al., 2004] and this has contributed to the diagnosis of more sensitizations to this substance [Martin-Gorgojo & Johansen, 2013]. One study showed significantly increased sensitivity between 2005 and 2010 using 0.5% IPBC in patch tests [Warshaw et al., 2013b].

See also
Ingredients of cosmetics

Iodopropynyl butylcarbamate
Ipbc.svg
Names
IUPAC name
3-Iodoprop-2-yn-1-yl butylcarbamate
Other names
3-Iodo-2-propynyl N-butylcarbamate; 3-Iodo-2-propynyl butylcarbamate; Iodocarb
Identifiers
CAS Number    
55406-53-6 check
3D model (JSmol)    
Interactive image
Abbreviations    IPBC
ChEBI    
CHEBI:83279 ☒
ChemSpider    
55933 check
ECHA InfoCard    100.054.188 
PubChem CID    
62097
UNII    
603P14DHEB check

Properties
Chemical formula    C8H12INO2
Molar mass    281.093 g·mol−1

IODOPROPYNYL BUTYLCARBAMATE
IODOPROPYNYL BUTYLCARBAMATE is classified as :
Preservative
CAS Number    55406-53-6
EINECS/ELINCS No:    259-627-5
Restriction (applies to EU only):    VI/56
COSING REF No:    34582
Chem/IUPAC Name:    3-Iodo-2-propynyl butylcarbamate

Iodopropynyl Butylcarbamate

What Is Iodopropynyl Butylcarbamate?
Iodopropynyl Butylcarbamate, also known as IPBC, is a white or slightly off-white crystalline powder that contains iodine. It is used in a wide variety of cosmetics and personal-care products

Why is Iodopropynyl Butylcarbamate used in cosmetics and personal care products?
Iodopropynyl Butylcarbamate prevents or retards bacterial growth, thereby protecting cosmetics and personal-care products from spoilage.

Follow this link for more information about how preservatives protect cosmetics and personal care products.

Scientific Facts: 
Iodopropynyl Butylcarbamate is an internationally recognized preservative that has been used for years because of a wide field of application. The need for a broad-spectrum and safe preservative system for cosmetics has led to the development of several combinations of IPBC with other preservatives effective against a wide variety of organisms. IPBC is also used as a preservative in household products, paints, cements and inks.

3-iodo-2-propynyl butylcarbamate is an off-white solid.

3-iodoprop-2-yn-1-yl butylcarbamate is a carbamate ester that is carbamic acid in which the nitrogen has been substituted by a butyl group and in which the hydrogen of the carboxy group is replaced by a 1-iodoprop-2-yn-3-yl group. A fungicide, it is used as a preservative and sapstain control chemical in wood products and as a preservative in adhesives, paints, latex paper coating, plastic, water-based inks, metal working fluids, textiles, and numerous consumer products. It has a role as a xenobiotic, an environmental contaminant and an antifungal agrochemical. It is a carbamate ester, an organoiodine compound, an acetylenic compound and a carbamate fungicide.

Molecular Weight of IPBC:    281.09 g/mol    Computed by PubChem 2.1 (PubChem release 2019.06.18)
XLogP3-AA of IPBC:    2.1    Computed by XLogP3 3.0 (PubChem release 2019.06.18)
Hydrogen Bond Donor Count of IPBC:    1    Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Hydrogen Bond Acceptor Count of IPBC:    2    Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Rotatable Bond Count of IPBC:    5    Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Exact Mass of IPBC:    280.99128 g/mol    Computed by PubChem 2.1 (PubChem release 2019.06.18)
Monoisotopic Mass of IPBC:    280.99128 g/mol    Computed by PubChem 2.1 (PubChem release 2019.06.18)
Topological Polar Surface Area of IPBC:    38.3 Ų    Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Heavy Atom Count of IPBC:    12    Computed by PubChem
Formal Charge of IPBC:    0    Computed by PubChem
Complexity of IPBC:    192    Computed by Cactvs 3.4.6.11 (PubChem release 2019.06.18)
Isotope Atom Count of IPBC:    0    Computed by PubChem
Defined Atom Stereocenter Count of IPBC:    0    Computed by PubChem
Undefined Atom Stereocenter Count of IPBC:    0    Computed by PubChem
Defined Bond Stereocenter Count of IPBC:    0    Computed by PubChem
Undefined Bond Stereocenter Count of IPBC:    0    Computed by PubChem
Covalently-Bonded Unit Count of IPBC:    1    Computed by PubChem
Compound  of IPBC Is Canonicalized    Yes

Iodopropynyl Butylcarbamate
Details
It's one of those things that help your cosmetics not to go wrong too soon, aka a preservative. Its strong point is being effective against yeasts and molds, and as a nice bonus seems to be non-comedogenic as well.

It is safe in concentrations of less than 0.1% but is acutely toxic when inhaled, so it's not the proper preservative choice for aerosol formulas like hairsprays. Used at 0.1%, Iodopropynyl Butylcarbamate has an extremely low rate of skin-irritation when applied directly for 24 hours (around 0.1% of 4,883 participants) and after 48 hours that figure was 0.5%, so it counts as mild and safe unless your skin is super-duper sensitive.

iodopropynyl butylcarbamate
Where is iodopropynyl butylcarbamate found?
Iodopropynyl butylcarbamate is a preservative used in cosmetics, wet wipes (toilet paper), and other personal care products. It is also used as a biocide in paints, primers, and industrial coolants and cooling lubricants.
How can you avoid contact with iodopropynyl butylcarbamate?
Avoid products that list any of the following names in the ingredients:

• Butyl-3-iodo-2-propynylcarbamate
• Carbamic acid, butyl-3-iodo-2-propynyl ester
• Iodopropynyl butylcarbamate
• 3-Iodo-2-propynyl butylcarbamate
• EPA Pesticide Chemical Code 107801
• BRN 2248232
• Caswell No. 501A
• EINECS 259-627-5
• HSDB 7314
• 3-Iodo-2-propynyl butyl carbamate

What are some products that may contain iodopropynyl butylcarbamate?
Baby Care
• Baby lotion
• Baby wash and shampoo
• Diaper rash cream
• Flushable moist wipes
Body Washes and Soaps
• Cleansing towelettes
• Makeup remover towelettes
Cosmetics
• Concealer
• Eye lash tint
• Liquid eye liner
Hair Dye
Hair Hair Styling Products
• Gel
• Hairspray
• Pomade
• Root lifter
Industrial Coolants and Cooling Lubricants
Lip Balm
Lotions and Skin Care Products
• Acne treatment
• Anti-itch cream
• Bar soap
• Body lotion
• Moisturizer
• Wrinkle cream
Paints and Stains
Shampoos and Conditioners
Shaving Creams and Gels
Sunscreens
Yard care
• Insect killer
• Weed killer

Iodopropynyl butylcarbamate (IPBC) is an internationally recognized chemical that has been used for years because of its wide field of application. Initially used as a water-based paint and wood preservative and then in metalworking fluids, its role has expanded into the more recent uses in cosmetic products. The need for a potent, broad-spectrum, and safe preservative system in cosmetics allowed for the discovery of several combinations of IPBC effective against a wide variety of organisms. Although IPBC has claimed to be safe when used at concentrations less than 0.1%, the introduction of IPBC into cosmetics has led to several reports labeling IPBC as a potential new contact allergen. As the use of this seemingly safe preservative becomes vast, an increased number of cases of IPBC-induced contact allergy is likely.