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C.I. Acid Green 3

HCID 20803
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Basic information

CAS
4680-78-8
Standard SMILES
CCN(Cc1cccc(S(=O)(=O)[O-])c1)c1ccc(C(=C2C=CC(=[N+](CC)Cc3cccc(S(=O)(=O)[O-])c3)C=C2)c2ccccc2)cc1.[Na+]
InChIKey
XKTMIJODWOEBKO-UHFFFAOYSA-M
Molecular formula
C37H35N2O6S2.Na
Average molar mass
690.8 g/mol
Monoisotopic mass
690.18342347

Overview

C.i. acid green 3 appears as a dull dark green powder. Used as a dye for silk or wool and biological stains.

Names & identifiers

Preferred name
C.I. Acid Green 3
IUPAC
sodium 3-[[N-ethyl-4-[[4-[ethyl-[(3-sulfonatophenyl)methyl]azaniumylidene]cyclohexa-2,5-dien-1-ylidene]-phenylmethyl]anilino]methyl]benzenesulfonate
English name
Acid green 3
Molecular formula
C37H37N2NaO6S2
Molecular weight
692.82

Names & synonyms

Acid Green 34680-78-8Guinea green BC.I. ACID GREEN 3Food Green 1FD&C Green no. 1Calcocid Green GAcid Green BLeather Green BAcidal Green GAcilan Green BAmacid Green B
Show more names
nsc5016nsc8684CI 42085MIDORI402Green GBfdcgreen1Aci Gree 3foodgreen1acidgreensafgreenno1
Fenazo Green LGuinea Green BAKiton Green FIntracid Green FKiton Green FCPontacyl Green BVondacid Green LAcid Green G

Database identifiers

CAS
4680-78-8
PubChem CID
20803
DTXSID
DTXSID3020671
ChEMBL
CHEMBL1333604
ChEBI

Properties

Computed structural properties

Topological polar surface area
137 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
7
Rotatable bonds
9
Heavy atoms
48
Formal charge
0
Complexity
1,250

Experimental & physicochemical properties

Chemical ClassesDyes -> Di- and Triaryl Dyes
Food AdditivesUse unspecified -> FDA Substance added to food
Color/Form · 3 items

A dull, dark green powder or bright crystalline solid

Maroon-purple powder

A dull, dark green powder or a bright, crystalline solid

Solubility · 2 items

In 2-methoxyethanol 20 mg/mL; in ethanol 9 mg/mL

In water, 30 mg/mL

DecompositionWhen heated to decomposition it emits very toxic fumes of /sulfur and nitrogen oxides as well as sodium monoxide/.
Melting Point255 °C (decomposes)
Physical Description · 3 items

C.i. acid green 3 appears as a dull dark green powder. Used as a dye for silk or wool and biological stains.

Wet Solid

Dark green solid; [Merck Index]

Other Experimental Properties · 2 items

Soluble in water to a green solution which becomes brownish-yellow on addition of hydrochloric acid and blackish-green with sodium hydroxide. An excess of sodium hydroxide decolorizes the solution.

Safety & regulation

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

Hazard information

Regulatory Information · 2 items

Chemical: Benzenemethanaminium, N-ethyl-N-[4-[[4-[ethyl[(3-sulfophenyl)methyl]amino]phenyl]phenylmethylene]-2,5-cyclohexadien-1-ylidene]-3-sulfo-, hydroxide, inner salt, sodium salt

Benzenemethanaminium, N-ethyl-N-[4-[[4-[ethyl[(3-sulfophenyl)methyl]amino]phenyl]phenylmethylene]-2,5-cyclohexadien-1-ylidene]-3-sulfo-, inner salt, sodium salt (1:1) is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of Benzenemethanaminium, N-ethyl-N-[4-[[4-[ethyl[(3-sulfophenyl)methyl]amino]phenyl]phenylmethylene]-2,5-cyclohexadien-1-ylidene]-3-sulfo-, inner salt, sodium salt (1:1) 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)

Hazards SummaryMay cause irritation; [MSDSonline]
Reactive GroupAmines, Phosphines, and Pyridines
Special ReportsCombes RD, Haveland-Smith RB; Mutat Res 98 (2): 101-248 (1982). A review of the genotoxicity of food drug and cosmetic colors and other azotriphenylmethane and xanthene dyes.
Reactivity Profile · 1 item

C.I. ACID GREEN 3 neutralizes acids in exothermic reactions to form salts plus water. May be incompatible with isocyanates, halogenated organics, peroxides, phenols (acidic), epoxides, anhydrides, and acid halides. May generate hydrogen, a flammable gas, in combination with strong reducing agents such as hydrides.

Air and Water ReactionsVery soluble in water. Forms a green solution, which becomes brownish-yellow by addition of HCl, and blackish-green with NaOH.

Safety & protection

Disposal Methods

Chemistry & industry

Pharmacology

Absorption, Distribution and ExcretionStudies in rats involving oral administration showed that only small amounts of the dye (< 5%) are absorbed and excreted unchanged in the bile. Following its iv injection in rats, about 75% of the dye was excreted in the bile within 4 hr.

Uses & manufacturing

Uses · 6 items

Used to dye wool, silk, leather, and paper; Also used in wood stains, biological stains, and, indicators; Used as a cosmetic in Western Europe (no contact with mucous membranes) and in Japan (external use only); [HSDB]

Discontinued use as a color additive for foods, drugs and cosmetics in the US in 1966; [HSDB]

Pulp and Paper Processing [Category: Industry]

Limited use as a dye for silk and wool fabrics; as biological stain

Use in barium and aluminum lakes that are used as pigments, in wood stain and in paper dyes.

Because of its low lightfastness ... has limited application in both dyeing and printing wool and silk (from an acid bath). Although it dyes fully chromed leather a brilliant green, this application ... is flawed by a low lightfastness.

ImpuritiesIn Japan, guinea green B has the following specifications: purity, 85% min; inorganic salt, 4% max; and water content, 10% max.
U.S. Production · 2 items

2023: 141,000 lb

(1973) approx 93,500 kg

Consumer UsesPigment
Methods of Manufacturing/Guinea Green B/ may be prepared commercially by condensing benzaldehyde with alpha-(N-ethylanilino)-meta-toluenesulfonic acid, followed by oxidation and conversion to the sodium salt.
Use Classification · 3 items

Food Additives -> COLOUR -> JECFA Functional Classes

Food Additives -> COLOUR -> JECFA Functional Classes

Related reactions

1 records
New reaction record
HRID 2357711 reaction equation
HRID 2357711As reactantuspto-grants-2010_07

Compound notes

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CHEBI:90112
UNII
4L2574620F
EC Number
225-132-8

Sparingly soluble in alcohol; it dissolves in concentrated sulfuric acid to a yellow solution which, when diluted with water, turns first yellowish-red, then green.

Physicochemical properties

Melting point
255 °C · 255 °C (dec.) (lit.)
Water Solubility
Soluble in water
solubility
DMSO (Slightly), Methanol (Slightly)
form
solid
Colour Index
42085 · 42085
color
Red to Dark blue to Black
λmax
618 nm · 618 nm
Merck
14 · 14,4575
Henry's Law Constant
2 · 2.0×1023 mol/(m3Pa) at 25℃, HSDB (2015)
Stability
Hygroscopic
InChIKey
XKTMIJODWOEBKO-UHFFFAOYSA-M
SMILES
[Na+].CCN(Cc1cccc(c1)S([O-])(=O)=O)c2ccc(cc2)\C(c3ccccc3)=C4\C=CC(\C=C4)=[N+](/CC)Cc5cccc(c5)S([O-])(=O)=O
CAS DataBase Reference
4680 · 4680-78-8
Substances Added to Food (formerly EAFUS)
1 · FD&C GREEN NO. 1--DELISTED
EWG's Food Scores
1 · 1
FDA UNII
4 L2574620F · 4L2574620F
IARC
3 · 3 (Vol. 16, Sup 7) 1987
EPA Substance Registry System
3 · C.I. Acid Green 3 (4680-78-8)
UNSPSC Code
12171500 · 12171500
NACRES
47 · NA.47
PPE
95 · Eyeshields, Gloves, type N95 (US)
WGK Germany
3 · 3
RTECS
4375000 · BQ4375000
TSCA
TSCA listed
HS Code
3204.12 · 3204.12.5090
Storage Class
13 · 13 - Non Combustible Solids
Hazardous Substances Data
4680 · 4680-78-8(Hazardous Substances Data)
Toxicity
50 orally · LD50 orally in rats: >2 g/kg (Lu, Lavalle)
· 1 item

SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational harm/injury/toxicity 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 and plant life; and conformance with environmental and public health regulations.

Toxicology

Ecotoxicity Values · 2 items

LC50; Species: Oryzias latipes (Medaka) length 2 cm, weight 0.2 g; Conditions: freshwater, static, 25 °C; Concentration: 1000000 ug/L for 24 hr /formulation/

LC50; Species: Oryzias latipes (Medaka) length 2 cm, weight 0.2 g; Conditions: freshwater, static, 25 °C; Concentration: 990000 ug/L for 48 hr /formulation/

Environmental Fate · 3 items

TERRESTRIAL FATE: Acid dyes, such as C.I. Acid Green 3, typically exhibit very low solubilities in octanol and have water solubilities that exceed 100 g/L. Therefore, these compounds would be expected to remain in the water column in the aquatic environment and show little affinity for organic matter(1) which suggests a potential to leach in soil(SRC). Volatilization of C.I. Acid Green 3 from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 4.9X10-29 atm-cu m/mole(SRC), using a fragment constant estimation method(2). C.I. Acid Green 3 not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 7.2X10-39 mm Hg at 25 °C(SRC), determined from a fragment constant method(2). Biodegradation data in soil were not available(SRC, 2011).

AQUATIC FATE: Acid dyes, such as C.I. Acid Green 3, typically exhibit very low solubilities in octanol and have water solubilities that exceed 100 g/L. Therefore, these compounds would be expected to remain in the water column in the aquatic environment and show little affinity for organic matter(1). Volatilization from water surfaces is not expected(2) based upon an estimated Henry's Law constant of 4.9X10-29 atm-cu m/mole(SRC), developed using a fragment constant estimation method(3). According to a classification scheme(4), an estimated BCF of 3(SRC), from an estimated log Kow of -3.20(3) and a regression-derived equation(3), suggests the potential for bioconcentration in aquatic organisms is low(SRC). Biodegradation data in water were not available(SRC, 2011).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), C.I. Acid Green 3, which has an estimated vapor pressure of 7.2X10-39 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase C.I. Acid Green 3 may be removed from the air by wet or dry deposition(SRC). C.I. Acid Green 3 absorbs light at wavelengths of 618 nm(4), and therefore may be susceptible to direct photolysis by sunlight(SRC).

Soil Adsorption/Mobility · 1 item

Acid dyes, such as C.I. Acid Green 3, typically exhibit very low solubilities in octanol and have water solubilities that exceed 100 g/L. Therefore, these compounds would be expected to remain in the water column in the aquatic environment and show little affinity for organic matter(1).

Natural Pollution SourcesC.I. Green 3 is not known to occur as a natural product(1).
Human Toxicity Excerpts · 1 item

/OTHER TOXICITY INFORMATION/ Most organic azo dyes are potential skin sensitizers, the most important of which are paraphenylenediamine and its analogs. Water soluble azo dyes are more likely to cause clinical sensitization than insoluble dyes. ... In addition to allergic eczematous contact dermatitis, color developing solutions have caused lichen planus like eruptions. /Organic dyes/

Artificial Pollution SourcesC.I. Acid Green 3's production and use as a dye(1) may result in its release to the environment through various waste streams(SRC).
Carcinogen Classification · 5 items

Guinea Green B

Group 3: Not classifiable as to its carcinogenicity to humans

Volume 16: (1978) Some Aromatic Amines and Related Nitro Compounds – Hair Dyes, Colouring Agents and Miscellaneous Industrial Chemicals

1987

1987

Environmental Bioconcentration · 1 item

An estimated BCF of 3 was calculated in fish for C.I. Acid Green 3(SRC), using an estimated log Kow of -3.20(1) and a regression-derived equation(1). According to a classification scheme(2), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).

Volatilization from Water/Soil · 1 item

The Henry's Law constant for C.I. Acid Green 3 is estimated as 4.9X10-29 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that C.I. Acid Green 3 is expected to be essentially nonvolatile from water surfaces(2). C.I. Acid Green 3's Henry's Law constant indicates that volatilization from moist soil surfaces is not expected occur(SRC). C.I. Acid Green 3 is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 7.2X10-39 mm Hg(SRC), determined from a fragment constant method(1).

Non-Human Toxicity Excerpts · 5 items

/LABORATORY ANIMALS: Acute Exposure/ Acid green was not damaging in rabbit eye test. It caused no more than slight transient irritation when tested on the eyes of rabbits, either by application of 4-8 mg of powdered dye to the conjunctival sac or by irrigating the surface of the eye for ten minutes with 0.02 M solution near neutrality after the epithelium has been removed to facilitate penetration. ...

/LABORATORY ANIMALS: Acute Exposure/ Arylmethane dyes which have been utilized as food colors, commercial dyes, laboratory stains and pH indicators were tested in the Salmonella/mammalian microsome mutagenicity assay. Eight mutagenic dyes were identified, including 5 food colors and 3 common laboratory stains; none of the 11 indicator dyes tested were mutagenic. The food color ... guinea green C.I. 42085 ... /was/ mutagenic in frameshift mutation detector strains TA98 and/or TA1538 and required metabolic activation. Most of the compounds gave weak mutagenic responses with Salmonella and were positive only within narrow dose ranges. Since conflicting results were obtained using dyes from different sources, minor dye components may have been responsible for their mutagenicity. Impurities in arylmethane colors still used in food and the toxicological role of such impurities merits further study.

/LABORATORY ANIMALS: Chronic Exposure or Carcinogenicity/ Toxicological testing of food dyes was conducted with experimental rats. ... Green-No-2 fed to rats at 2 percent of the diet for two years caused no tumors. With the remaining four dyes, Green-No-1 (Guinea-Green-B), Red-No-2 (amaranth), Red-No-3 (erythrosine), and Yellow-No-5 (tartrazine), no distant tumors were caused by the injections; except for one with Green-No-1, none appeared at the point of injection. Some of the animals survived, and feeding studies on some of the dyes were continued.

/LABORATORY ANIMALS: Chronic Exposure or Carcinogenicity/ The results of feeding rats, dogs and mice diets containing Guinea Green B, Light Green SF Yellowish or Fast Green FCF for 2 yr are reported. ... The three green colorings, Guinea Green B, Light Green SF Yellowish and Fast Green FCF, were each fed at dietary levels of 0.0, 1.0 and 2.0 % to groups of two male and two female beagle dogs for 2 yr. Ten of the 12 dogs fed Guinea Green B survived in good clinical condition. A male at 2 % was killed after 1 yr when he became moribund and a female at 1% died after 5 months. Both non-survivors showed generalized inanition-type atrophy of the bone marrow, fat, skeletal muscle, adrenal cortex, lymphatic tissue and the gastric mucosa. Moderate periportal fatty metamorphosis of the liver was observed in a male survivor on 2 %. ...

For more Non-Human Toxicity Excerpts (Complete) data for C.I. ACID GREEN 3 (11 total), please visit the HSDB record page.

Evidence for CarcinogenicityNo data are available in humans. Limited evidence of carcinogenicity in animals. OVERALL EVALUATION: Group 3: The agent is not classifiable as to its carcinogenicity to humans.
Environmental Abiotic DegradationAcid dyes, such as C.I. Acid Green 3, readily dissociate in water(1). C.I. Acid Green 3 absorbs light at wavelengths of 618 nm(2), and therefore may be susceptible to direct photolysis by sunlight(SRC).

Safety data

PPE
Eyeshields, Gloves, type N95 (US)
wgk
3
tsca
TSCA listed
rtecs
BQ4375000
hs_code
3204.12.5090
Toxicity
LD50 orally in rats: >2 g/kg (Lu, Lavalle)
Storage Class
13 - Non Combustible Solids
Hazardous Substances Data
4680-78-8(Hazardous Substances Data)

Food Additives -> COLOUR -> JECFA Functional Classes

General Manufacturing Information · 3 items

Benzenemethanaminium, N-ethyl-N-[4-[[4-[ethyl[(3-sulfophenyl)methyl]amino]phenyl]phenylmethylene]-2,5-cyclohexadien-1-ylidene]-3-sulfo-, inner salt, sodium salt (1:1): ACTIVE

Guinea Green B has been produced commercially in the USA for over fifty years. Guinea green B was first produced commercially in Japan in 1940. It is believed that there is one producer currently; however, no production has been reported since 1973, when 200 kg were manufactured. There are no Japanese exports or imports of this chemical.

Color additives were initially regulated in the United States under the U.S. Department of Agriculture's (USDA) Bureau of Chemistry. In 1906, the Food and Drugs Act was passed by Congress, which prohibited the use of poisonous or deleterious colors in confectionery and the coloring or staining of food to conceal damage or inferiority. In 1927, responsibility of the Food and Drugs Act was transferred to FDA. Increasing government oversight, the Federal Food, Drug, and Cosmetic Act (FFDCA) was passed in 1938 and established the three following categories for colors: FD&C: colors used in foods, drugs and cosmetics; D&C: colors used in drugs and cosmetics when in contact with mucous membranes or ingested; and Ext. D&C: colors used in products applied externally.

Applications · 3 items

UsesGuinea Green B has been used as a pharmacophore compound to study its inhibitory action on papillomavirus type 16 E6 protein.

UsesLimited use as a dye for silk and wool fabrics; as biological stain.

General DescriptionA dull dark green powder. Used as a dye for silk or wool and biological stains.

Preparation methods

PreparationBenzaldehyde (1 Moore) and 3-(Ethyl(phenyl)amino)methyl)benzenesulfonic acid (2 Moore) condensation, will product oxidation, and then translate into sodium salt.

Upstream & downstream products

Upstream raw materials

BenzaldehydeN-Ethyl-N-benzylaniline-3'-sulfonic acid
Additional notes · 1 item

DefinitionChEBI: An organic sodium salt having 3-[(ethyl{4-[(4-{ethyl[(3-sulfonatophenyl)methyl]amino}phenyl)(phenyl)methylidene]cyclohexa-2,5-dien-1-ylidene}azaniumyl)methyl]benzene-1-sulfonate. Used as a substitute for Light green SF yellowish in Masson's trichrome, alth ugh it is prone to fade. Previously used as a food dye but is now no longer approved.