基本情報
- CAS
464-48-2- 標準SMILES
CC1(C)[C@H]2CC[C@]1(C)C(=O)C2- InChIKey
DSSYKIVIOFKYAU-OIBJUYFYSA-N- 分子式
- C10H16O
- 平均分子量
- 152.23 g/mol
- 単同位体質量
- 152.12011513
概要
L-camphor appears as colorless or white crystals. Fragrant and penetrating odor. Slightly bitter and cooling taste. Odor index at 68 °F: 40. Flash point 149 °F. Burns with a bright, smoky flame. Sublimes appreciably at room temperature and pressure; 14% sublimes within 60 minutes at 176 °F and 12 mmHg. (NTP, 1992)
名称と識別子
- 優先名称
- Camphor, (-)-
- IUPAC
- (1S,4S)-1,7,7-trimethylbicyclo[2.2.1]heptan-2-one
- 現地名
- (-)-カンファー
- 英語名
- (-)-CAMPHOR
- 分子式
- C10H16O
- 分子量
- 152.23
名称と別名
名称をさらに表示
データベース識別子
- CAS
464-48-2- PubChem CID
- 444294
- DTXSID
DTXSID8022036- ChEMBL
CHEMBL2252949- ChEBI
CHEBI:15397- UNII
- 213N3S8275
- EC Number
- 207-354-7
- Nikkaji
- J67.498B
物性
構造計算による物性
- XLogP
- 2.2
- 極性表面積
- 17.1 Ų
- 水素結合供与体数
- 0
- 水素結合受容体数
- 1
- 回転可能結合数
- 0
- 重原子数
- 11
- 形式電荷
- 0
- 複雑度
- 217
実験および物理化学的性質
Melting Point
353.5 °F (NTP, 1992)
178-180
Vapor Pressure
1 mmHg at 106.7 °F (NTP, 1992)
0.18 [mmHg]
Physical Description
L-camphor appears as colorless or white crystals. Fragrant and penetrating odor. Slightly bitter and cooling taste. Odor index at 68 °F: 40. Flash point 149 °F. Burns with a bright, smoky flame. Sublimes appreciably at room temperature and pressure; 14% sublimes within 60 minutes at 176 °F and 12 mmHg. (NTP, 1992)
Colorless to white solid with a strong fragrant odor; [CAMEO] White powder; [Sigma-Aldrich MSDS]
物理化学的性質
- 融点
- 177 · 177-179 °C(lit.)
- 沸点
- 204 °C · 204 °C(lit.)
- 比旋光度
- -44.8 ° · -44.8° (20/D)(EtOH)
- 比重(密度)
- 0.99 · 0.990
- 蒸気密度
- 5.24 · 5.24 (vs air)
- 蒸気圧
- 4 mm · 4 mm Hg ( 70 °C)
- 屈折率
- -44 ° · -44 ° (C=20, EtOH)
- 闪点
- 148 °F · 148 °F
- 貯蔵温度
- Sealed in dry,Room Temperature
- 溶解性
- 30 mg/ml; · DMF: 30 mg/ml; DMSO: 20 mg/ml; Ethanol: 30 mg/ml; Ethanol:PBS (pH 7.2)(1:2): 0.33 mg/ml
- 外見
- 結晶または結晶性粉末の付着
- 色
- 白から黄色
- 比重
- 0.9853 · 0.9853 (18℃)
- 臭い (Odor)
- 10 %。樟脳 · ジプロピレングリコール中10.00%。樟脳
- においのタイプ
- 樟脳のような
- 爆発限界(explosive limit)
- 0.6 · 0.6-4.5%(V)
- 水溶解度
- 水に溶ける。 (0.34 g/L) 20°Cで
- Merck
- 14 · 14,1732
- BRN
- 4291747 · 4291747
- 安定性
- 安定。強力な還元剤、強力な酸化剤、および塩素系溶剤とは相溶しません。光を避けてください。
- InChI
- 1S/C10H16O/c1-9(2)7-4-5-10(9,3)8(11)6-7/h7H,4-6H2,1-3H3/t7-,10+/m0/s1
- InChIKey
- DSSYKIVIOFKYAU-OIBJUYFYSA-N
- SMILES
- [H][C@]12CC[C@](C)(C(=O)C1)C2(C)C
- LogP
- 2.089 · 2.089 (est)
- CAS データベース
- 464 · 464-48-2(CAS DataBase Reference)
- EPAの化学物質情報
- l-Camphor (464-48-2)
化学的性質
化学的特性white crystals
安全と法規制
GHS分類
GHS Classification
Danger
H228 (35.5%): Flammable solid [Danger Flammable solids]
P203, P210, P240, P241, P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P318, P319, P321, P332+P317, P337+P317, P362+P364, P370+P378, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 138 reports by companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
危険有害性情報
Regulatory Information
Chemical: Bicyclo[2.2.1]heptan-2-one, 1,7,7-trimethyl-, (1S)-
(1S)-(-)-Camphor: Does not have an individual approval but may be used under an appropriate group standard
Health Hazards
SYMPTOMS: Ingestion of this compound may cause nausea, vomiting, vertigo, mental confusion, delirium, convulsions, coma, respiratory failure or death. It may also cause a burning sensation, coughing, wheezing, laryngitis, shortness of breath, headache, severe irritation and possible destruction to the tissues of the mucous membranes, upper respiratory tract, eyes and skin. Other symptoms may include congestion and edematous changes in the gastrointestinal tract, kidneys and brain. Ingestion may result in burning in the mouth and throat, epigastric pain, thirst, feeling of tension, dizziness, irrational behavior, unconsciousness, rigidity, rapid pulse, slow respiration, twitching of the facial muscles and muscular spasms. Other symptoms may include flickering, darkening or veiling of vision, noises in the ears and weakness. Exposure to this compound may also result in a feeling of warmth, depression of the central nervous system, difficult breathing, a characteristic breath odor and anuria. Colic may also be a symptom of exposure. Other symptoms may include eye irritation, sore throat, excitement, fever, bluish lips, pale face, loss of sense of smell and agitation.
Hazards Summary
May cause severe skin, eye, mucous membrane, and upper respiratory tract irritation; May cause CNS depression and other nervous system effects; Harmful by ingestion, inhalation, and skin absorption; [NTP] Causes convulsions in oral lethal-dose studies of rats; [RTECS] Camphor used topically during pregnancy in not likely to cause teratogenic effects; [TERIS] An irritant; Readily absorbed through skin; Targets the liver, kidney, and nerves; Ingestion may cause vertigo, confusion, clonic convulsions, coma, respiratory failure, and death; [Sigma-Aldrich MSDS] See Camphor, synthetic.
Reactivity Profile
L-CAMPHOR may be sensitive to heat and direct sunlight. Incompatible with strong oxidizing agents, strong reducing agents and chlorinated solvents. Also incompatible with potassium permanganate. Salts of any kind should not be added to it in water. Reacts violently with chromic anhydride (NTP, 1992).
安全と保護具
First Aid
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.
Nonfire Spill Response
SMALL SPILLS AND LEAKAGE: Should a spill occur while you are handling this chemical, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with 60-70% ethanol and transfer the dampened material to a suitable container. Use absorbent paper dampened with 60-70% ethanol to pick up any remaining material. Seal the absorbent paper, and any of your clothes, which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 60-70% ethanol 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.
毒性情報
安全データ
- wgk
- 1
- tsca
- TSCA listed
- rtecs
- EX1250000
- ridadr
- UN 2717 4.1/PG 3
- hs_code
- 29142910
- risk_code
- 11-36/37/38
- 化審法
- (4)-308, (4)-601
- hazard_code
- F,Xi
- safety_code
- 16-26
- hazard_class
- 4.1
- packing_group
- III
- 自然発火温度
- 870 °F
- Hazard Classifications
- Eye Irrit. 2Flam. Sol. 2Skin Irrit. 2STOT SE 3
- ストレージクラス
- 4.1B - Flammable solid hazardous materials
化学と産業
薬理情報
Pharmacodynamics
Camphor exerts an analgesic action when applied topically by producing a warm sensation. It excites and desensitizes sensory nerves by activating heat-sensitive TRP vanilloid subtype 1 (TRPV1) and TRPV3 receptors. (S)-camphor is reported to exert a weaker action on TRPV1 channels, which is thought to be a result of tachyphylaxis, which is the reduction of the response to multiple stimulations.
Mechanism of Action
TRPV3 cation channels are molecular sensors that play a role in nociception and thermosensation by inducing thermal sensation and heat-induced hyperalgesia. Camphor interacts with TRPV3 channels via pore-region cysteine residues, leading to channel activation and a rise in intracellular calcium levels. Camphor also activates TRPV1 and a TRPV1-like current in dorsal root ganglion (DRG) neurons but inhibits the ankyrin-repeat TRP 1 (TRPA1) channel expressed in most nociceptive DRG neurons, which is responsible for the detection of temperature. The precise role of TRPA1 current inhibition on the analgesic properties of camphor is unclear. Repeated stimulation by camphor leads to sensitization of the TRPV1 and TRPV3 channels, resulting in desensitization, or reduced channel response that likely leads to the analgesic effects of camphor. Camphor also activates cold-sensitive transient receptor potential melastatin 8 (TRPM8) and sensitizes cold-induced calcium transients, which explains the cooling effect of camphor following dermal application. Additionally, camphor was shown to inhibit the TRPM8 receptor response to menthol.
Absorption, Distribution and Excretion
Absorption of camphor in the mucous membranes and the gastrointestinal tract is rapid, and peak concentration following oral ingestion occurs within 5 to 90 minutes.
Camphor undergoes renal excretion.
Volume of distribution of camphor is 2 to 4 L/kg. Camphor and its metabolites are relatively fat-soluble thus may accumulate in adipose and other tissues. Camphor ingested by mothers was present in amnionic fluid, cord and fetal blood and fetal brain, liver and kidneys.
No pharmacokinetic data available.
用途と製造
Uses
Naturally occurring form of camphor; Used in organic synthesis and as an odorant, flavoring agent, moth repellent, preservative, and plasticizer in cosmetics; Also used as a topical analgesic and antipruritic; [Merck Index] Used as a plasticizer for cellulose esters and ethers, to make plastics, cymene, and incense, in lacquers, varnishes, explosives, embalming fluids, pyrotechnics, and insect repellents; [NTP]
Painting (Pigments, Binders, and Biocides) [Category: Paint]
応用分野
用途有機合成原料。
使用(1S)-(-)-Camphor is used as chiral intermediate and chiral auxiliary precursor. It is used in the synthesis of high-potency sweeteners. It acts as catalytic agent and petrochemical additive.
一般的な説明Colorless or white crystals. Fragrant and penetrating odor. Slightly bitter and cooling taste. Odor index at 68°F: 40. Flash point 149°F. Burns with a bright, smoky flame. Sublimes appreciably at room temperature and pressure; 14% sublimes within 60 minutes at 176°F and 12 mm Hg.
調製方法
純化方法Crystallise it from EtOH, 50% EtOH/water, MeOH, or pet ether or from glacial acetic acid by addition of water. It can be sublimed (50o/14mm) and also fractionally crystallised from its own melt. It is steam volatile. It should be stored in tight containers as it is appreciably volatile at room temperature. The solubility is 0.1% (H2O), 100% (EtOH), 173% (Et2O) and 300%
上流・下流製品情報
上流原料
下流製品
サプライヤー100 社
補足説明
定義ChEBI: The S-enantiomer of camphor.
関連反応
化合物ノート
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