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Home > Encyclopedia > 2-Hydroxy-1,4-naphthoquinone

2-Hydroxy-1,4-naphthoquinone

2-Hydroxy-1,4-naphthoquinone structure

2-Hydroxy-1,4-naphthoquinone 

structure
  • CAS No:

    83-72-7

  • Formula:

    C10H6O3

  • Chemical Name:

    2-Hydroxy-1,4-naphthoquinone

  • Synonyms:

    1,4-Naphthalenedione,2-hydroxy-;1,4-Naphthoquinone,2-hydroxy-;2-Hydroxy-1,4-naphthalenedione;C.I. 75480;C.I. Natural Orange 6;Flower of Paradise;Henna;Lawsone;Mehendi;Mendi;2-Hydroxy-1,4-naphthoquinone;2-Hydroxynaphthoquinone;Henna (dye);Q 0;Pakarli;NSC 8625;1,4-Dihydro-1,4-dioxo-2-hydroxynaphthalene;NSC 27285;NSC 52500;Quino Power LSN;Quinoexter 2014;Quinoexter QE 2014;2-Hydroxy-1,4-dihydronaphthalene-1,4-dione;1985594-94-2

  • Categories:

    Cosmetic Ingredient  >  Skin Conditioning

Description

Lawsone is a naphthoquinone dye isolated from leaves of Lawsonia inermis that shows antimicrobial and antioxidant activity[1].


2-hydroxy-1,4-naphthoquinone appears as yellow prisms or yellow powder. (NTP, 1992)


2-hydroxy-1,4-naphthoquinone appears as yellow prisms or yellow powder. (NTP, 1992)|Lawsone is 1,4-Naphthoquinone carrying a hydroxy function at C-2. It is obtained from the leaves of Lawsonia inermis. It has a role as a protective agent and an antifungal agent. It is a tautomer of a naphthalene-1,2,4-trione.

2-Hydroxy-1,4-naphthoquinone Basic Attributes

174.15

174.15

1565260

201-496-3

TLH4A6LV1W

27285|8625

DTXSID2025428

2914690090

Characteristics

54.4

1.55

Yellow Crystalline Powder

1.5±0.1 g/cm3

195.5 °C (decomp)

339.9±42.0 °C at 760 mmHg

173.6±24.4 °C

1.681

H2O: 2g/L (20 ºC)

Keep tightly closed. Store in a cool dry place.

Insoluble in water.

Ketones

Phenols, such as 2-HYDROXY-1,4-NAPHTHOQUINONE, do not behave as organic alcohols, as one might guess from the presence of a hydroxyl (-OH) group in their structure. Instead, they react as weak organic acids. Phenols and cresols are much weaker as acids than common carboxylic acids (phenol has pKa = 9.88). These materials are incompatible with strong reducing substances such as hydrides, nitrides, alkali metals, and sulfides. Flammable gas (H2) is often generated, and the heat of the reaction may ignite the gas. Heat is also generated by the acid-base reaction between phenols and bases. Such heating may initiate polymerization of the organic compound. Phenols are sulfonated very readily (for example, by concentrated sulfuric acid at room temperature). The reactions generate heat. Phenols are also nitrated very rapidly, even by dilute nitric acid. Nitrated phenols often explode when heated. Many of them form metal salts that tend toward detonation by rather mild shock.

Safety Information

II

NONH for all modes of transport

3

36/37/38-68-36-22

26-37/39-36/37/39-36

QL8200000

Xi,Xn

Stable. Combustible. Incompatible with strong oxidizing agents.

P261-P305 + P351 + P338

H315-H319-H335

Flash point data for this chemical are not available but it is probably combustible. (NTP, 1992)

|Warning|H302 (15.22%): Harmful if swallowed [Warning Acute toxicity, oral]|P201, P202, P261, P264, P270, P271, P280, P281, P301+P312, P302+P352, P304+P340, P305+P351+P338, P308+P313, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 46 companies from 5 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Fires involving this compound should be controlled using a dry chemical, carbon dioxide, foam or Halon extinguisher. (NTP, 1992)

SMALL SPILLS AND LEAKAGE: If you spill this chemical, FIRST REMOVE ALL SOURCES OF IGNITION, then dampen the solid spill material with toluene, then transfer the dampened material to a suitable container. Use absorbent paper dampened with toluene to pick up any remaining material. Your contaminated clothing and absorbent paper should be sealed in a vapor-tight plastic bag for eventual disposal. Solvent-wash all contaminated surfaces with toluene followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned. STORAGE PRECAUTIONS: You should store this material in a refrigerator. (NTP, 1992)

RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)

Drug Information

Chemical or physical agents that protect the skin from sunburn and erythema by absorbing or blocking ultraviolet radiation. (See all compounds classified as Sunscreening Agents.)|Substances that destroy fungi by suppressing their ability to grow or reproduce. They differ from FUNGICIDES, INDUSTRIAL because they defend against fungi present in human or animal tissues. (See all compounds classified as Antifungal Agents.)|Chemicals and substances that impart color including soluble dyes and insoluble pigments. They are used in INKS; PAINTS; and as INDICATORS AND REAGENTS. (See all compounds classified as Coloring Agents.)|Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. (See all compounds classified as Enzyme Inhibitors.)

ACUTE/CHRONIC HAZARDS: This compound may be absorbed through the skin and can cause skin irritation. (NTP, 1992)

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop. SKIN: IMMEDIATELY flood affected skin with water while removing and isolating all contaminated clothing. Gently wash all affected skin areas thoroughly with soap and water. If symptoms such as redness or irritation develop, IMMEDIATELY call a physician and be prepared to transport the victim to a hospital for treatment. INHALATION: IMMEDIATELY leave the contaminated area; take deep breaths of fresh air. If symptoms (such as wheezing, coughing, shortness of breath, or burning in the mouth, throat, or chest) develop, call a physician and be prepared to transport the victim to a hospital. Provide proper respiratory protection to rescuers entering an unknown atmosphere. Whenever possible, Self-Contained Breathing Apparatus (SCBA) should be used; if not available, use a level of protection greater than or equal to that advised under Protective Clothing. INGESTION: DO NOT INDUCE VOMITING. If the victim is conscious and not convulsing, give 1 or 2 glasses of water to dilute the chemical and IMMEDIATELY call a hospital or poison control center. Be prepared to transport the victim to a hospital if advised by a physician. If the victim is convulsing or unconscious, do not give anything by mouth, ensure that the victim's airway is open and lay the victim on his/her side with the head lower than the body. DO NOT INDUCE VOMITING. IMMEDIATELY transport the victim to a hospital. (NTP, 1992)

2-hydroxy-1,4-naphthoquinone

2-Hydroxy-1,4-naphthoquinone Use and Manufacturing

Methods of Manufacturing

Ammonium 1, 2-naphthoquinone-4-sulfonate and sulfur are reacted in methanol to obtain methoxynaphthoquinone, which is then hydrolyzed with sodium hydroxide to obtain 2-hydroxy-1, 4-naphthoquinone. The yield is 58-65%.

Uses

An antimicrobial antioxidant dye isolated from Henna.

1,4-Naphthalenedione, 2-hydroxy-: INACTIVE

Cosmetics -> Bulking; Hair dyeing; Skin conditioning|Environmental transformation -> Pesticide transformation products (metabolite, successor)

HN is a known environmental transformation product of Quinoclamine.

Computed Properties

Molecular Weight:174.15
XLogP3:0.9
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Exact Mass:174.031694049
Monoisotopic Mass:174.031694049
Topological Polar Surface Area:54.4
Heavy Atom Count:13
Complexity:291
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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