基本情報
- CAS
99-83-2- 標準SMILES
CC1=CCC(C(C)C)C=C1- InChIKey
OGLDWXZKYODSOB-UHFFFAOYSA-N- 分子式
- C10H16
- 平均分子量
- 136.23 g/mol
- 単同位体質量
- 136.12520051
概要
Alpha-phellandrene is one of a pair of phellandrene cyclic monoterpene double-bond isomers in which both double bonds are endocyclic (cf. alpha-phellandrene, where one of them is exocyclic). It has a role as a volatile oil component, an antimicrobial agent and a plant metabolite. It is a cyclohexadiene and a phellandrene.
名称と識別子
- 優先名称
- alpha-PHELLANDRENE
- IUPAC
- 2-methyl-5-propan-2-ylcyclohexa-1,3-diene
- 現地名
- p-メンタ-1,5-ジエン
- 英語名
- alpha-Phellandrene
- 分子式
- C10H16
- 分子量
- 136.23
名称と別名
ALPHA-PHELLANDRENE99-83-2p-Mentha-1,5-dieneMenthadienealpha-FellandreneDihydro-p-cymenealpha Phellandrene5-Isopropyl-2-methyl-1,3-cyclohexadienePhellandrene, alpha-4-Isopropyl-1-methyl-1,5-cyclohexadiene1-Isopropyl-4-methyl-2,4-cyclohexadiene1-Methyl-4-isopropyl-1,5-cyclohexadiene
名称をさらに表示
p-メンタ-1,5-ジエン5-イソプロピル-2-メチル-1,3-シクロヘキサジエン3-メチル-6-イソプロピルシクロヘキサ-1,3-ジエンメンタジエン2-メチル-5-イソプロピル-1,3-シクロヘキサジエン1-イソプロピル-4-メチル-2,4-シクロヘキサジエン2-メチル-5-(1-メチルエチル)-1,3-シクロヘキサジエンΑ‐フェランドレン(-)-2-メチル-5-イソプロピル-1,3-シクロヘキサジエンα-phellandreneA-PHELLANDRENEl-PhellandreneFEMA 28561,3-Cyclohexadiene, 2-methyl-5-(1-methylethyl)-alpha-phellandereneα-PheL
2-Methyl-5-isopropyl-1,3-cyclohexadiene5-isopropyl-2-methylcyclohexa-1,3-diene2-methyl-5-(1-methylethyl)-1,3-cyclohexadieneFEMA No. 2856DTXSID4047593alpha-Phellandrene (natural)2-methyl-5-(propan-2-yl)cyclohexa-1,3-dieneHSDB 1130
データベース識別子
- CAS
99-83-2- PubChem CID
- 7460
- DTXSID
DTXSID4047593- ChEMBL
CHEMBL3188459、CHEMBL455041- ChEBI
CHEBI:50035- UNII
- 49JV13XE39
- EC Number
- 202-792-5
- Nikkaji
- J55.716A
物性
構造計算による物性
- XLogP
- 3.2
- 極性表面積
- 0 Ų
- 水素結合供与体数
- 0
- 水素結合受容体数
- 0
- 回転可能結合数
- 1
- 重原子数
- 10
- 形式電荷
- 0
- 複雑度
- 161
実験および物理化学的性質
Chemical ClassesBiological Agents -> Plant Oils and Extracts
FragrancesFragrance Ingredient (alpha-Phellandrene) -> IFRA transparency List
LogP4.58
Food AdditivesFLAVORING AGENT OR ADJUVANT -> FDA Substance added to food
Density0.845-0.855
Flavoring AgentsEU Flavoring substances
Color/FormCOLORLESS OIL
Solubility
PRACTICALLY INSOL IN WATER; SOL IN ETHER /D- & L-FORMS/
5000 mg/L @ 25 °C (exp)
Insoluble in water; soluble in oils
Soluble (in ethanol)
Boiling Point175 °C
Melting Point249.00 °C. @ 760.00 mm Hg
Vapor Pressure1.4 [mmHg]
Refractive Index1.471-1.477
物理化学的性質
- 沸点
- 185.55 °C · 185.55°C (rough estimate)
- 比重(密度)
- 0.85 g/mL · 0.85 g/mL at 25 °C(lit.)
- FEMA
- 2856 · 2856 | ALPHA-PHELLANDRENE
- 屈折率
- 20 · n20/D 1.474(lit.)
- 闪点
- 117 °F · 117 °F
- 貯蔵温度
- 30 °C · Store below +30°C.
- 溶解性
- Benzene: Soluble; Chloroform: Soluble
- 外見
- An oil
- 融点
- 25 °C · <25 °C
- 色
- Colorless to light yellow
- 臭い (Odor)
- 10 %。シトラス · ジプロピレングリコール中10.00%。シトラス ハーブ テルペン グリーン ウッディ ペッパー
- においのタイプ
- テルペン
- 由来生物
- synthetic
- JECFA Number
- 1328 · 1328
- Merck
- 13 · 13,7277
- Henry's Law Constant
- 1.8 · 1.8×10-4 mol/(m3Pa) at 25℃, Plyasunov and Shock (2000)
- 安定性
- Light Sensitive, Temperature Sensitive
- 主な用途
- フレーバーそして香料
- 化粧品成分の機能
- 香料
- InChI
- 1S/C10H16/c1-8(2)10-6-4-9(3)5-7-10/h4-6,8,10H,7H2,1-3H3
- InChIKey
- OGLDWXZKYODSOB-UHFFFAOYSA-N
- SMILES
- CC(C)C1CC=C(C)C=C1
- LogP
- 4.43 · 4.43
- CAS データベース
- 99 · 99-83-2(CAS DataBase Reference)
- EPAの化学物質情報
- 1 · 1,3-Cyclohexadiene, 2-methyl-5-(1-methylethyl)- (99-83-2)
化学的性質
化学的特性α-Phellandrene has a pleasant, fresh, citrus, peppery odor with a discrete mint note. This compound is also reported as having a minty, herbaceous odor.
安全と法規制
安全情報は参考情報です。供給元の安全データシート（SDS）、適用法令、専門家による評価に代わるものではありません。
GHS分類
GHS Classification
Danger
H226 (> 99.9%): Flammable liquid and vapor [Warning Flammable liquids]
P210, P233, P240, P241, P242, P243, P280, P301+P316, P303+P361+P353, P331, P370+P378, P403+P235, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 1722 reports by companies from 17 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Danger
H304: May be fatal if swallowed and enters airways [Danger Aspiration hazard]
危険有害性情報
Regulatory Information
Chemical: 1,3-Cyclohexadiene, 2-methyl-5-(1-methylethyl)-
Commission Regulation (EC) No 1565/2000 (Repealed by Com. Implementing Reg. (EU) No 872/2012)
1,3-Cyclohexadiene, 2-methyl-5-(1-methylethyl)- is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 1,3-Cyclohexadiene, 2-methyl-5-(1-methylethyl)- 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)
1,3-Cyclohexadiene, 2-methyl-5-(1-methylethyl)-: Does not have an individual approval but may be used under an appropriate group standard
Other Safety InformationEvaluation - Chemicals that are unlikely to require further regulation to manage risks to environment
Hazards Summary
A strong irritant; [Hawley] Emergency treatment: Irritants; [HSDB] Can cause diarrhea and vomiting after ingestion; [Merck Index] Safe when used as a flavoring agent in food; [JECFA] An irritant; Can be absorbed through skin; May cause skin and respiratory sensitization; [Aldrich MSDS]
FDA Requirements121.1164 LIMITATIONS: SYNTHETIC FLAVOR
Peroxide Forming Chemical
alpha-Phellandrene
B*: Compounds that form peroxides on concentration (distillation/evaporation)
Bretherick's
An explosion occured during distillation. See Bretherick's.
Bodendorf, K., Arch. Pharm., 1933, 271, 28
Hazard Classes and Categories
Flam. Liq. 3 (> 99.9%)
Aspiration hazard - category 1
毒性情報
Natural Pollution Sources
NATURAL OCCURRENCE AND CHEMISTRY OF ALPHA-PHELLANDRENE.
NATURAL OCCURRENCE: COMPOSED 16.25% OF PLANT.
NATURAL OCCURRENCE.
NATURAL OCCURRENCE OF ALPHA-PHELLANDRENE.
For more Natural Pollution Sources (Complete) data for ALPHA-PHELLANDRENE (6 total), please visit the HSDB record page.
Human Toxicity Excerpts
...CAN BE IRRITATING TO, & ABSORBED THROUGH, SKIN. INGESTION CAN CAUSE VOMITING, DIARRHEA.
HYPERSENSITIVITY FOUND DUE TO SENSITIZING PROPERTIES OF 3 INGREDIENTS: ALPHA-PINENE, LIMONENE, & PHELLANDRENE IN DENTAL PREPN.
Non-Human Toxicity ExcerptsALPHA-PHELLANDRENE APPLIED FULL STRENGTH TO INTACT OR ABRADED RABBIT SKIN FOR 24 HR UNDER OCCLUSION WAS MODERATELY IRRITATING.
法規制情報
FDA Requirements121.1164 LIMITATIONS: SYNTHETIC FLAVOR
安全データ
- wgk
- 3
- tsca
- TSCA listed
- rtecs
- OS8080000
- ridadr
- UN 2319 3/PG 3
- 毒性
- LD50 orally in Rabbit: 5700 mg/kg
- hs_code
- 3301 90 10
- risk_code
- 10-22-36/37/38-43
- 消防法
- 危-4-2-III
- hazard_code
- Xn,F
- safety_code
- 16-26-36/37
- hazard_class
- 3.2
- packing_group
- III
- Hazard Classifications
- Asp. Tox. 1Flam. Liq. 3
- ストレージクラス
- 3 - Flammable liquids
- 有毒物質データの
- 99-83-2(Hazardous Substances Data)
化学と産業
薬理情報
Metabolism/Metabolites
...ALPHA-PHELLANDRENE...IS METABOLIZED INTO P-MENTHANE DERIV, PHELLANDRIC ACID, BY REDN OF 1 OF THE DOUBLE BONDS OF THE CYCLOHEXADIENE RING...
IN SHEEP, ALPHA-PHELLANTHRENE APPARENTLY UNDERGOES REDN OF ONE DOUBLE BOND & OXIDN OF METHYL GROUP TO GIVE PHELLANDRAL, FURTHER OXIDIZED TO PHELLANDRIC ACID, EXCRETED IN URINE. SUGGESTED THAT IT IS 2,3,5-TRIHYDROXYLATED TO P-MENTHOTRIOL & EXCRETED AS GLUCURONIDE.
Absorption, Distribution and Excretion...ABSORBED THROUGH, SKIN.
Cellular LocationsExtracellular
用途と製造
Uses
Found in Ceylon ginger oil, Seychelles cinnamon oil, and eucalyptus oil; Used in flavors and perfumes; [Hawley] Used as a chemical intermediate; [HSDB]
FLAVORING; PERFUMERY
CHEM INTERMEDIATE
U.S. Production2023: 630 lb
Industry UsesFragrance
Methods of Manufacturing
ISOLATION OF L-FORM FROM ESSENTIAL OILS OF EUCALYPTUS DIVES SCHAU & E PHELLANDRA BAKER & SMITH, MYRTACEAE: SMITH ET AL, J CHEM SOC 123, 1657 (1923). ISOLATION OF D-FORM FROM OIL OF BITTER FENNEL (FOENICULUM VULGARE MILL, UMBELLIFERAE): WALLACH, ANN 336, 9 (1904).
Household ProductsInformation on 5 consumer products that contain Alpha-Phellandrene in the following categories is provided:
Use Classification
Fragrance Ingredients
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavoring Agents -> JECFA Flavorings Index
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
Flavouring Agent -> FLAVOURING_AGENT -> JECFA Functional Classes
General Manufacturing Information
Not Known or Reasonably Ascertainable
1,3-Cyclohexadiene, 2-methyl-5-(1-methylethyl)-: ACTIVE
STRUCTURE: SEMMLER, BER 36, 1749 (1903). SYNTHESIS: READ, STOREY, J CHEM SOC 1930, 2770. CONFIGURATION: BURGSTAHLER ET AL, J AM CHEM SOC 83, 4660 (1961). REVIEW: JL SIMONSEN, THE TERPENES VOL 1 (UNIVERSITY PRESS, CAMBRIDGE, 2ND ED, 1947) PP 193-204.
MONOCYCLIC TERPENE OCCURRING AS (A) D- & (B) L-OPTICAL ISOMERS.
NATURAL OCCURRENCE AND CHEMISTRY OF ALPHA-PHELLANDRENE.
IN DILL ALPHA-PHELLANDRENE CONTENT WAS HIGHEST @ NIGHT, DECR IN DAYLIGHT WITH COMPETITION OF CARVONE PRODN.
応用分野
天然物の起源The d-form has been reported found in the essential oils of bitter fennel, Ceylon cinnamon leaves, star anise, Curcuma longa and other essential oils; the l-form has been reported found in various eucalyptus oils, orange peel oil, angelica, Lantana camara and other oils. Reported found in over 100 foods and beverages including apricot, many citrus peel oils and juices, black currants, papaya, raspberry, strawberry, carrot, celery leaves and seed, bell pepper, tomato, cinnamon, cumin seed, ginger, Mentha oils, nutmeg, pepper, mace, parsley, thyme, Gruyere cheese, cured pork, hop oil, beer, tea, pecan, passion fruit, sweet and wild marjoram, mango, parsnip, cardamom, coriander seed, gin, litchi, dill herb and seed, lovage leaf and seed, caraway, juniper berry, laurel, bitter and sweet fennel, myrtle leaf and berry, sage, nectarine, pimento leaf and berry and mastic gum leaf oil.
使用α-Phellandrene is an essential oil component, found to have bactericidal activity.
一般的な説明α-Phellandrene is monoterpene reported to be one of the aroma compounds of black (Piper nigrum) and white ‘‘Ashanti pepper′′ (Piper guineense). It also occurs in the leaves of basil.
上流・下流製品情報
上流原料
補足説明
定義ChEBI: One of a pair of phellandrene cyclic monoterpene double-bond isomers in which both double bonds are endocyclic (cf. alpha-phellandrene, where one of them is exocyclic).
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