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Home> Encyclopedia >Food Colorants>Pharmaceutical Intermediates>Organic Intermediate
Nonanoic acid structure
Nonanoic acid structure

Nonanoic acid

Iupac Name:nonanoic acid
CAS No.: 112-05-0
Molecular Weight:158.23802
Modify Date.: 2022-11-06 11:38
Introduction: Nonanoic acid (also known as pelargonic acid; chemical formula: CH3(CH2)7COOH) is a kind of organic carboxylic acid compound. It is naturally existed in the oil of pelargonium in the form of esters. It is commonly used in conjunction with glyphosate which is a kind of non-selective herbicide in order to obtain a quick burn-down effect in the control of weeds in turfgrass. It is also a potent antifungal agent which can inhibit spore germination and mycelial growth of pathogenic fungi. Its synthetic esters, such as methyl nonanoate can be used as flavorings. Moreover, it can also be used in the preparation of plasticizers and lacquers. It can also be potentially used for the treatment of seizures. View more+
1. Names and Identifiers
1.1 Name
Nonanoic acid
1.2 Synonyms

Acid C9, Pelargonic acid Acid C9,Pelargonic acid EINECS 203-931-2 MFCD00004433 n-Nonanoic acid N-NONYLIC ACID NO0NOIC ACID NONANE nonanic acid nona-N-methyl-4,4',4''-methanetriyl-tri-anilinium,tris iodide Nona-N-methyl-4,4',4''-methantriyl-tri-anilinium,Tris-jodid Nonanoic acid (Pelargonic acid) Nonanoic acid (Pelargonic) NONANOIC ACID FOR SYNTHESIS Nonanoic acid,Acid C9, Pelargonic acid NONANOIC ACID/PELARGONIC ACID NONANOICACID(PELARGONICACID) NONANOIC-D4 ACID noncarboxylic acid Nonoic acid nonyloic acid Pelargonic Acid

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1.3 CAS No.
112-05-0
1.4 CID
8158
1.5 EINECS(EC#)
203-931-2
1.6 Molecular Formula
C9H18O2 (isomer)
1.7 Inchi
InChI=1S/C9H18O2/c1-2-3-4-5-6-7-8-9(10)11/h2-8H2,1H3,(H,10,11)
1.8 InChIkey
FBUKVWPVBMHYJY-UHFFFAOYSA-N
1.9 Canonical Smiles
CCCCCCCCC(=O)O
1.10 Isomers Smiles
CCCCCCCCC(=O)O
2. Properties
2.1 Density
0.906
2.1 Melting point
12.5℃
2.1 Boiling point
254℃
2.1 Refractive index
1.4299-1.4339
2.1 Flash Point
114℃
2.2 Precise Quality
158.13100
2.2 PSA
37.30000
2.2 logP
2.82160
2.2 Solubility
0.3g/l
2.3 Viscosity
8.08 mPa.sec at 20 °C
2.4 VaporDensity
5.5 (vs air)
2.5 Appearance
clear, oily liquid with an unpleasant, rancid odor
2.6 Storage
Ambient temperatures.
2.7 Chemical Properties
clear colorless liquid
2.8 Color/Form
Colorless, oily liquid at ordinary temp; crystallizes when cooled
Yellowish oil
2.9 Decomposition
When heated to decomposition it emits acrid smoke and irritating fumes.
2.10 Heat of Combustion
-5,456.1 kJ/mol
2.11 Odor
FATTY ODOR
2.12 Odor Threshold
Aroma threshold values: Detection: 3 to 9 ppm.
2.13 PH
4.4 (0.1g/l, H2O, 25℃)
2.14 pKa
4.96(at 25℃)
2.15 Water Solubility
NEGLIGIBLE
2.16 Spectral Properties
Index of refraction: 1.4343 at 20 deg C/D
IR: 60 (Sadtler Research Laboratories Prism Collection)
1H NMR: 9 (Sadtler Research Laboratories Spectral Collection)
13C NMR: 362 (Johnson & Jankowski, Carbon-13 NMR Spectra, John WIley & Sons, NY)
MASS: 5504 (NIST/EPA/MSDC Mass Spectral database, 1990 version)
2.17 Stability
Stable under normal temperatures and pressures.
2.18 StorageTemp
2-8°C
3. Use and Manufacturing
3.1 Agricultural Uses
Herbicide, Fungicide: Pelargonic acid occurs naturally in many plants andanimals. It is used to control the growth of weeds and as ablossom thinner for apple and pear trees. It is also used asa food additive; as an ingredient in solutions used to commerciallypeel fruits and vegetables
3.2 Definition
ChEBI: 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.
3.3 Potential Exposure
Pelargonic acid, a naturally occurringfatty acid herbicide/fungicide. It is used to control thegrowth of weeds and as a blossom thinner for apple andpear trees. It is also used as a food additive; as an ingredientin solutions used to commercially peel fruits andvegetables; in the manufacture of lacquers, plastics andpharmaceuticals.
3.4 Purification Methods
Esterify the acid with ethylene glycol and distil the ester. (This removes dibasic acids as undistillable residues.) The acid is regenerated by hydrolysing the ester in the usual way and is distilled in vacuo. [Beilstein 2 IV 1018.]
3.5 Usage
The primary uses of this acid are in organic synthesis and inthe manufacture of lacquers, plastics, pharmaceuticals, syntheticodors and flavorings, gasoline additives, flotationagents, lubricants, and vinyl plasticizers. Nonanoic acidhas found some use in pharmaceutical preparations and asa topical bactericide and fungicide. It is also used inherbicides.
3.6 Waste Disposal
Do not discharge into drainsor sewers. Dispose of waste material as hazardous wasteusing a licensed disposal contractor to an approved landfill.Contact a licensed disposal facility about surplus andnon-recyclable solutions. Burn in a chemical incineratorequipped with an afterburner and scrubber. Extra care mustbe exercised as the material in an organic solvent is highlyflammable. Consult with environmental regulatory agenciesfor guidance on acceptable disposal practices. Incinerationwith effluent gas scrubbing is recommended. Containersmust be disposed of properly by following package labeldirections or by contacting your local or federal environmentalcontrol agency, or by contacting your regional EPAoffice. Nonanoic acid Preparation Products And Raw materials Raw materials
4. Safety and Handling
4.1 Symbol
GHS05;
4.1 Hazard Codes
C
4.1 Signal Word
DANGER
4.1 Risk Statements
R34
4.1 Safety Statements
S26;S28;S36/37/39;S45
4.1 Exposure Standards and Regulations
Nonanoic acid is a food additive permitted for direct addition to food for human consumption as a synthetic flavoring substance and adjuvant in accordance with the following conditions: a) they are used in the minimum quantity required to produce their intended effect, and otherwise in accordance with all the principles of good manufacturing practice, and 2) they consist of one or more of the following, used alone or in combination with flavoring substances and adjuvants generally recognized as safe in food, prior-sanctioned for such use, or regulated by an appropriate section in this part.
4.2 Packing Group
III
4.2 Octanol/Water Partition Coefficient
log Kow = 3.42
4.3 Other Preventative Measures
SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.
SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. Quality assurance to ascertain the completeness of the cleaning procedures should be implemented before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at end of shift, but should remain at employee's place of work for cleaning.
Agricultural Use Requirements: Use this product only in accordance with its labeling and with the Worker Protection Standard... . Do not enter or allow worker entry into treated areas during the restricted entry interval (REI) of 12 hours. ./Scythe herbicide (57% pelargonic acid)/
Do not get in eyes, on skin or on clothing. Avoid breathing spray mist. Wash thoroughly with soap and water after handling. Pemove contaminated clothing and wash clothing before reuse. /Scythe herbicide (57% pelargonic acid)/
Worker Protection Standard Uses: Discard clothing and other absorbent materials that have been drenched or heavily contaminated with this product's concentrate. Do not reuse them. Follow manufacturer's instructions for cleaning/maintaining personal protective equipment (PPE). If no such instructions for washables, use detergent and hot water. Keep and wash PPE separate from other laundry../Scythe herbicide (57% pelargonic acid)/
Users should wash hands before eating, drinking, chewing gum, using tobacco or using the toilet. Remove clothing immediately if pesticide gets inside. Then wash thoroughly and put on clean clothing. Remove personal protective equipment (PPE) immediately after handling this product. Wash the outside of gloves before removing. As soon as possible, wash thoroughly and change into clean clothing. /Scythe herbicide (57% pelargonic acid)/
If in eyes: hold eye open and rinse slowly and gently with water for 15-20 minutes. Remove contact lenses, if present, after the first 5 minutes, then continue rinsing eye. ... If on skin or clothing: Take off contaminated clothing. Rinse skin immediately with plenty of water for 15-20 minutes. ... /Scythe herbicide (57% pelargonic acid)/
Care must be exercised to avoid contact of spray with foilage of desirable turfgrasses, trees, shrubs, or other desirable vegetation since damage can result. /Scythe herbicide (57% pelargonic acid)/
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4.4 Hazard Class
8
4.4 Hazard Declaration
H314
4.4 DisposalMethods
SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure 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, aquatic, and plant life; and conformance with environmental and public health regulations.
Do not contaminate water, food, or feed by ... disposal. ... Pesticide disposal:: Wastes resulting from the use of this product must be disposed of on site or at an approved waste disposal facility. Container disposal: Do not reuse empty container. Triple rinse, then offer for recycling or reconditioning, or puncture and dispose of in a sanitary landfill or by incineration, or if allowed by state and local authorities, by burning. If burned, stay out of smoke. /Scythe herbicide (57% pelargonic acid)/
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4.5 RIDADR
UN 3265
4.5 FirePotential
Combustible
4.6 Safety Profile
Poison by intravenousroute. Moderately toxic by ingestion. Asevere skin and eye irritant. When heated todecomposition it emits acrid smoke andirritating fumes.
4.7 Caution Statement
P280-P303 + P361 + P353-P304 + P340 + P310-P305 + P351 + P338
4.7 Formulations/Preparations
Grade: Technical 99%
Econosan Acid Sanitizer: Active Ingredients 8.50% Phosphoric acid, 10.0% Propionic acid, 9.50% Sulfuric acid, 3.00% Capric acid; 3.00% Nonanoic acid
Mandate Plus: Active Ingredients 1.09% Capric acid and 6.30% Nonanoic acid
MON 78999 Herbicide: Active Ingredients 2.00% Glyphosate, isopropylamine salt, and 2.00% Nonanoic acid
RD 1653 Herbicide: Active Ingredients 1.00% Glyphosate, isopropylamine salt; 0.017% Imazaquin, monoammonium salt; 2.00% Nonanoic acid
RD 1662 Herbicide: Active Ingredients 1.00% Glyphosate, isopropylamine salt; 0.100% Triethylamine triclopyr; 2.00% Nonanoic acid
Scythe Herbicide: Active Ingredient 57.0% Nonanoic acid
West Agro Acid Sanitizer: Active Ingredients 28.5% Phosphoric acid, 10.0% Propionic acid, 3.00% Capric acid, 3.00% Nonanoic acid
EC.
Biopesticide (Non-systemic, broad-spectrum contact herbicide): Ammonium nonanoate (PC code 031802; the end use product contains 40.0% by weight ammonium nonanoate; Trade name: Racer Concentrate; Formulation Type: Liquid)
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4.8 Incompatibilities
Heated vapors may form explosive mixturewith air. May react violently with strong oxidizers,bromine, 90% hydrogen peroxide, phosphorus trichloride,silver powders or dust. Incompatible with strong bases andsilver compounds; mixture with some silver compoundsmay form explosive salts of silver oxalate.
4.9 WGK Germany
1
4.9 RTECS
RA6650000
4.9 Protective Equipment and Clothing
Worker Protection Standard (WPS) Uses: Some materials that are chemical-resistant to this product are listed below. If you want more options, follow the instructions for category E on an EPA chemical resistance category selection chart. Applicators and other handlers who handle this pesticide for any use covered by the WPS ... must wear: Coveralls worn over short-sleeved shirt and short pants; chemical-resistant gloves such as barrier laminate, nitrile rubber, or neoprene rubber; chemical-resistant footwear plus socks; protective eyewear (goggles, face shield or safety glasses) /Scythe herbicide (57% pelargonic acid)/
Agricultural Use Requirements: Personal protective equipment required for early entry to treated areas that is permitted under the Worker Protection Standard and that involves contact with anything that has been treated, such as plants, soil, or water, include: Coveralls worn over short-sleeved shirt and short pants; chemical-resistant gloves such as barrier laminate, nitrile rubber, or neoprene rubber; chemical-resistant footwear plus socks; protective eyewear (goggles, face shield or safety glasses... /Scythe herbicide (57% pelargonic acid)/
Non-WPS Uses: Applicators and other handlers who handle this pesticide for any use not covered by the Worker Protection Standard ... must wear: Long-sleeved shirt and long pants; chemical-resistant gloves such as barrier laminate, nitrile rubber, or neoprene rubber; protective eyewear (goggles, face shield or safety glasses) /Scythe herbicide (57% pelargonic acid)/
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4.10 Report

Reported in EPA TSCA Inventory.

4.11 Skin, Eye, and Respiratory Irritations
Pelargonic acid is a skin and eye irritant.
Causes substantial but temporary eye injury. Causes skin irritation. ... /Scythe herbicide (57% pelargonic acid)/
4.12 Safety

Hazard Codes: CorrosiveC
Risk Statements: 34 
R34:Causes burns.
Safety Statements: 26-28-36/37/39-45-28A 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S28:After contact with skin, wash immediately with plenty of soap-suds. 
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection. 
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) 
S28:After contact with skin, wash immediately with plenty of soap-suds.
RIDADR: UN 3265 8/PG 3
WGK Germany: 1
RTECS: RA6650000
HazardClass: 8
PackingGroup: III
HS Code: 29159080
Poison by intravenous route. Moderately toxic by ingestion. A severe skin and eye irritant. When heated to decomposition it emits acrid smoke and irritating fumes.

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4.13 Specification

 Nonanoic acid (CAS NO.112-05-0) is also named as 1-Octanecarboxyic acid ; 1-Octanecarboxylic acid ; 4-02-00-01018 (Beilstein Handbook Reference) ; AI3-04164 ; BRN 1752351 ; Cirrasol 185A ; Cirrasol 185a ; EPA Pesticide Chemical Code 217500 ; Emfac 1202 ; FEMA No. 2784 ; HSDB 5554 ; Hexacid C-9 ; NSC 62787 ; Nonylic acid ; Pelargic acid ; Pelargon ; Pelargon [Russian] ; Pelargonic acid ; UNII-97SEH7577T ; n-Nonanoic acid ; n-Nonoic acid ; n-Nonylic acid . Nonanoic acid (CAS NO.112-05-0) is a clear, oily liquid with an unpleasant, rancid odor. It is nearly insoluble in water, but very soluble in chloroform, ether, and hexane. Nonanoic acid is a fatty acid which occurs naturally as esters in the oil of pelargonium.

4.14 Toxicity
1.    

skn-rbt 500 mg/24H MOD

    FCTXAV    Food and Cosmetics Toxicology. 16 (1978),839.
2.    

eye-rbt 91 mg SEV

    EMERY*    Emery Industries, Inc., Data Sheets .(Cincinnati, OH.: )1964,S3B.
3.    

skn-gpg 100% SEV

    FCTXAV    Food and Cosmetics Toxicology. 16 (1978),839.
4.    

orl-rat LDLo:3200 mg/kg

    14CYAT    Industrial Hygiene and Toxicology. 2 (1963),1788.
5.    

orl-mus LD50:15 g/kg

    GISAAA    Gigiena i Sanitariya. 42 (3)(1977),99.
6.    

ivn-mus LD50:224 mg/kg

    APTOA6    Acta Pharmacologica et Toxicologica. 18 (1961),141.
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5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Skin irritation, Category 2

Eye irritation, Category 2

Hazardous to the aquatic environment, long-term (Chronic) - Category Chronic 3

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word

Warning

Hazard statement(s)

H315 Causes skin irritation

H319 Causes serious eye irritation

H412 Harmful to aquatic life with long lasting effects

Precautionary statement(s)
Prevention

P264 Wash ... thoroughly after handling.

P280 Wear protective gloves/protective clothing/eye protection/face protection.

P273 Avoid release to the environment.

Response

P302+P352 IF ON SKIN: Wash with plenty of water/...

P321 Specific treatment (see ... on this label).

P332+P313 If skin irritation occurs: Get medical advice/attention.

P362+P364 Take off contaminated clothing and wash it before reuse.

P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.

P337+P313 If eye irritation persists: Get medical advice/attention.

Storage

none

Disposal

P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

8. Other Information
8.0 Usage
Nonanoic acid is used in the preparation of plasticizers and lacquers. It is commonly used in conjunction with glyphosate, for a quick burn-down effect in the control of weeds in turfgrass.
8.1 Merck
14,7070
8.2 BRN
1752351
8.3 Description
Nonanoic acid (also known as pelargonic acid; chemical formula: CH3 (CH2)7COOH) is a kind of organic carboxylic acid compound. It is naturally existed in the oil of pelargonium in the form of esters. It is commonly used in conjunction with glyphosate which is a kind of non-selective herbicide in order to obtain a quick burn-down effect in the control of weeds in turfgrass. It is also a potent antifungal agent which can inhibit spore germination and mycelial growth of pathogenic fungi. Its synthetic esters, such as methyl nonanoate can be used as flavorings. Moreover, it can also be used in the preparation of plasticizers and lacquers. It can also be potentially used for the treatment of seizures.
8.4 References
https://en.wikipedia.org/wiki/Nonanoic_acid
http://www.abcam.com/nonanoic-acid-pelargonic-acid-ab143891.html
8.5 Description
Nonanoic acid , also called pelargonic acid, is an organic compound composed of a nine - carbon chain terminating in a carboxylic acid with structural formula CH3(CH2)7COOH. Nonanoic acid forms esters—nonanoates. It is a clear, oily liquid with an unpleasant, rancid odor. It is nearly insoluble in water, but very soluble in chloroform, ether, and hexane.
Its refractive index is 1.4322. Its critical point is at 712 K ( 439 °C ) and 2.35 MPa.
8.6 Chemical Properties
clear colorless liquid
8.7 Chemical Properties
Colorless or yellowish, combustible, oily liquid. Faint odor.
8.8 Chemical Properties
Nonanoic acid has a fatty, characteristic odor and a corresponding unpleasant taste. May be prepared by oxidation of methylnonyl ketone; by oxidation of oleic acid; or from heptyl iodide via malonic ester synthesis.
8.9 Chemical Properties
Nonanoic acid has a fatty, characteristic odor and a corresponding unpleasant taste. This compound is also reported as having a cheese, waxy flavor
8.10 Originator
Pellar,Crookes Barnes, US ,1960
8.11 Occurrence
Nonanoic acid is a fatty acid which occurs naturally as esters in the oil of pelargonium. Synthetic esters, such as methyl nonanoate, are used as flavorings.
Nonanoic 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 nonanoic acid, ammonium nonanoate, is used as an herbicide.
8.12 Uses
The primary uses of this acid are in organic synthesis and in the manufacture of lacquers, plastics, pharmaceuticals, synthetic odors and flavorings, gasoline additives, flotation agents, lubricants, and vinyl plasticizers. Nonanoic acid has found some use in pharmaceutical preparations and as a topical bactericide and fungicide. It is also used in herbicides.
8.13 Uses
Intermediates of Liquid Crystals
8.14 Uses
In the production of hydrotropic salts (hydrotropic salts form aqueous solutions which dissolve sparingly soluble substances to a greater extent than water); in the manufacture of lacquers, plastics.
8.15 Definition
ChEBI: 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.
8.16 Manufacturing Process
A body of liquid, 18 inches high, comprising a 35% (by weight) solution of technical (95%) oleic acid in n-propanol, is maintained at a temperature of 86°C in a reactor. The solution also contains dissolved therein 0.042% by weight of cobalt, in the form of cobalt naphthenate. From the bottom of the reactor very fine bubbles of air are passed into and through the solution at the rate of about 0.3 cubic feet per minute, measured at standard conditions, per square foot for 72 hours. The gases leaving the reactor are first passed through an ice water reflux condenser and then vented to the atmosphere. At the end of the 72 hour period the reaction mixture is separated into its components. It is found that 60% of the oleic acid has been consumed in the reaction. For each pound of oleic acid consumed there are obtained 0.30 pound of azelaic acid (representing an efficiency of 46%, calculated on the basis that the technical oleic acid is 100% oleic acid), 0.13 pound of pelargonic acid (representing an efficiency of 23%) and 0.21 pound of 9,10dihydroxystearic acid (representing an efficiency of 19%).
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8.17 Therapeutic Function
Fungicide
8.18 Aroma threshold values
Detection: 3 to 9 ppm
8.19 Taste threshold values
Taste characteristics at 10 ppm: fatty, waxy, and cheesy with a mild, sweet, creamy background
8.20 Synthesis Reference(s)
Journal of the American Chemical Society, 93, p. 195, 1971 DOI: 10.1021/ja00730a033
Organic Syntheses, Coll. Vol. 2, p. 474, 1943
Tetrahedron Letters, 9, p. 5689, 1968
8.21 General Description
Nonanoic acid occurs naturally in Pelargonium L′Her. It one of the flavor constituents of cooked rice, acerola fruit, licorice and yogurt.
9. Computational chemical data
  • Molecular Weight: 158.23802g/mol
  • Molecular Formula: C9H18O2
  • Compound Is Canonicalized: True
  • XLogP3-AA: null
  • Exact Mass: 158.130679813
  • Monoisotopic Mass: 158.130679813
  • Complexity: 99.7
  • Rotatable Bond Count: 7
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 2
  • Topological Polar Surface Area: 37.3
  • Heavy Atom Count: 11
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count: 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Isotope Atom Count: 0
  • Covalently-Bonded Unit Count: 1
  • CACTVS Substructure Key Fingerprint: AAADceBwMAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAGgAACAAACACAgAACCAAAAgAIAACQCAAAAAAAAAAAAAEAAAAAABIAAAAAQAAEAAAAAAGIyKCAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==
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12. Realated Product Infomation