lactic acid menthyl ester | 59259-38-0

• 物质功能分类: 有机原料 - 羧酸类化合物及衍生物 - 羧酸酯及其衍生物
• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: lactic acid menthyl ester
• 英文别名: Menthyl lactate；2-hydroxypropionic acid-L-menthyl；(-)-Menthyl lactate；[(1R,2S,5R)-5-methyl-2-propan-2-ylcyclohexyl] 2-hydroxypropanoate
• CAS: 59259-38-0
• 化学式: C₁₃H₂₄O₃
• 分子量: 228.332
• InChiKey: UJNOLBSYLSYIBM-SGUBAKSOSA-N

物化性质

• 熔点：
  40 °C
• 比旋光度：
  -74 º (c=10, EtOH)
• 沸点：
  310.14°C (rough estimate)
• 密度：
  -80
• 闪点：
  128 °C
• 溶解度：
  DMSO（微溶）、乙醇（微溶）
• LogP：
  3.20
• 物理描述：
  Solid
• 保留指数：
  1473
• 稳定性/保质期：
  遵照规定使用和储存，则不会发生分解。

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

安全信息

• 危险品标志：
  T
• 安全说明：
  S24/25
• 危险类别码：
  R25
• 海关编码：
  2918110000
• 储存条件：
  存放于阴凉干燥处即可。

SDS

Name:	(-)-Menthyl lactate 98% Material Safety Data Sheet
Synonym:	Lactic acid menthyl ester
CAS:	59259-38-0

Section 1 - Chemical Product MSDS Name:(-)-Menthyl lactate 98% Material Safety Data Sheet
Synonym:Lactic acid menthyl ester

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Section 2 - COMPOSITION, INFORMATION ON INGREDIENTS

CAS#	Chemical Name	content	EINECS#
59259-38-0	(-)-Menthyl lactate	98	261-678-3

Hazard Symbols: None Listed.
Risk Phrases: None Listed.

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Section 3 - HAZARDS IDENTIFICATION
EMERGENCY OVERVIEW
The toxicological properties of this material have not been fully investigated.
Potential Health Effects
Eye:
May cause eye irritation.
Skin:
May cause skin irritation.
Ingestion:
May cause irritation of the digestive tract. The toxicological properties of this substance have not been fully investigated.
Inhalation:
May cause respiratory tract irritation. The toxicological properties of this substance have not been fully investigated.
Chronic:
No information found.

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Section 4 - FIRST AID MEASURES
Eyes: Flush eyes with plenty of water for at least 15 minutes, occasionally lifting the upper and lower eyelids. Get medical aid.
Skin:
Get medical aid. Flush skin with plenty of water for at least 15 minutes while removing contaminated clothing and shoes. Wash clothing before reuse.
Ingestion:
Never give anything by mouth to an unconscious person. Get medical aid. Do NOT induce vomiting. If conscious and alert, rinse mouth and drink 2-4 cupfuls of milk or water.
Inhalation:
Remove from exposure and move to fresh air immediately. If not breathing, give artificial respiration. If breathing is difficult, give oxygen. Get medical aid.
Notes to Physician:

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Section 5 - FIRE FIGHTING MEASURES
General Information:
As in any fire, wear a self-contained breathing apparatus in pressure-demand, MSHA/NIOSH (approved or equivalent), and full protective gear. During a fire, irritating and highly toxic gases may be generated by thermal decomposition or combustion.
Extinguishing Media:
Use water spray, dry chemical, carbon dioxide, or appropriate foam.

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Section 6 - ACCIDENTAL RELEASE MEASURES
General Information: Use proper personal protective equipment as indicated in Section 8.
Spills/Leaks:
Sweep up, then place into a suitable container for disposal. Avoid generating dusty conditions. Provide ventilation.

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Section 7 - HANDLING and STORAGE
Handling:
Wash thoroughly after handling. Remove contaminated clothing and wash before reuse. Use with adequate ventilation. Avoid contact with eyes, skin, and clothing. Avoid ingestion and inhalation.
Storage:
Store in a tightly closed container. Store in a cool, dry, well-ventilated area away from incompatible substances.

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Section 8 - EXPOSURE CONTROLS, PERSONAL PROTECTION
Engineering Controls:
Facilities storing or utilizing this material should be equipped with an eyewash facility and a safety shower. Use adequate ventilation to keep airborne concentrations low.
Exposure Limits CAS# 59259-38-0: Personal Protective Equipment Eyes: Wear appropriate protective eyeglasses or chemical safety goggles as described by OSHA's eye and face protection regulations in 29 CFR 1910.133 or European Standard EN166.
Skin:
Wear appropriate protective gloves to prevent skin exposure.
Clothing:
Wear appropriate protective clothing to prevent skin exposure.
Respirators:
A respiratory protection program that meets OSHA's 29 CFR 1910.134 and ANSI Z88.2 requirements or European Standard EN 149 must be followed whenever workplace conditions warrant respirator use.

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Section 9 - PHYSICAL AND CHEMICAL PROPERTIES

Physical State: Solid
Color: white
Odor: None reported.
pH: Not available.
Vapor Pressure: Not available.
Viscosity: Not available.
Boiling Point: Not available.
Freezing/Melting Point: 40.00 - 42.00 deg C
Autoignition Temperature: Not applicable.
Flash Point: 165 deg C ( 329.00 deg F)
Explosion Limits, lower: Not available.
Explosion Limits, upper: Not available.
Decomposition Temperature: Not available.
Solubility in water: slightly soluble
Specific Gravity/Density: Not available.
Molecular Formula: C13H24O3
Molecular Weight: 228.33

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Section 10 - STABILITY AND REACTIVITY
Chemical Stability:
Stable under normal temperatures and pressures.
Conditions to Avoid:
Incompatible materials, acids, strong oxidants.
Incompatibilities with Other Materials:
Oxidizing agents.
Hazardous Decomposition Products:
Irritating and toxic fumes and gases.
Hazardous Polymerization: Has not been reported.

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Section 11 - TOXICOLOGICAL INFORMATION
RTECS#:
CAS# 59259-38-0 unlisted.
LD50/LC50:
Not available.
Carcinogenicity:
(-)-Menthyl lactate - Not listed by ACGIH, IARC, or NTP.

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Section 12 - ECOLOGICAL INFORMATION

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Section 13 - DISPOSAL CONSIDERATIONS
Dispose of in a manner consistent with federal, state, and local regulations.

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Section 14 - TRANSPORT INFORMATION

IATA
Not regulated as a hazardous material.
IMO
Not regulated as a hazardous material.
RID/ADR
Not regulated as a hazardous material.

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Section 15 - REGULATORY INFORMATION

European/International Regulations
European Labeling in Accordance with EC Directives
Hazard Symbols: Not available.
Risk Phrases:
Safety Phrases:
S 24/25 Avoid contact with skin and eyes.
WGK (Water Danger/Protection)
CAS# 59259-38-0: No information available.
Canada
CAS# 59259-38-0 is listed on Canada's DSL List.
CAS# 59259-38-0 is not listed on Canada's Ingredient Disclosure List.
US FEDERAL
TSCA
CAS# 59259-38-0 is not listed on the TSCA inventory.
It is for research and development use only.

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SECTION 16 - ADDITIONAL INFORMATION
N/A

制备方法与用途

产品描述

乳酸孟酯（英文名：Menthyl Lactate, 简称ML），又称乳酸薄荷酯，常温下为白色晶体。它是一种薄荷衍生物，具有轻微的薄荷香气，尝起来几乎没有味道，但却能带来持久而令人愉悦的清凉感。这种成分被广泛认为是极好的清凉剂，且没有不良反应如灼烧感、刺激感和刺痛感等，因此在化妆品、护肤品、食品、饮料、口腔护理产品、糖果、牙膏、医药以及烟草等多个行业均有应用。

以往配方师设计清凉型产品时只能选择薄荷，但其挥发性和刺激性较强，导致清凉效果短暂且强烈，还常掩盖其他香精的香气。乳酸孟酯因其特性，成为理想的选择。

本品易溶于醇类等有机溶剂，略溶于水。使用时建议先将其预溶解在酒精、丙二醇等溶剂中或溶于香精后再添加至产品（具体添加量根据建议用量确定）。

常效清凉剂

1. 碱性应用：(-)-薄荷甘油缩酮 (63187-91-7)
2. 酸性应用：(-)-薄荷醇乳酸酯 (59259-38-0)

毒性与使用限量 毒性

GRAS（FEMA）。

使用限量

根据FEMA (1998)标准，不同产品中的添加量有所不同：

• 焙烤制品：60～250 mg/kg
• 无醇饮料：30～120 mg/kg
• 含醇饮料：100～400 mg/kg
• 早餐谷物：15～60 mg/kg
• 胶姆糖：1000～2000 mg/kg
• 干酪：15～60 mg/kg
• 调味品：100~400 mg/kg
• 糖霜：500～2000 mg/kg
• 冷饮：30～120 mg/kg
• 水果冰：100～400 mg/kg
• 明胶、布丁：200～800 mg/kg
• 调味汁：25～100 mg/kg
• 硬糖：1000~2000 mg/kg
• 代乳品：15～60 mg/kg
• 速溶咖啡和茶：1004400 mg/kg
• 乳制品：2004800 mg/kg
• 加工水果：100～400 mg/kg
• 小吃食品：25～100 mg/kg
• 软糖：500~2000 mg/kg
• 汤料：25～100 mg/kg

用途

乳酸孟酯是一种长效无味的清凉剂，适用于薄荷香精的调配。

反应信息

• 作为反应物：
  描述：

  lactic acid menthyl ester 在 双氧水 、 sodium bromide 、 一水合肼 作用下， 以 二氯甲烷 为溶剂， 反应 1.5h， 以96.63%的产率得到2-Oxo-propionic acid (1R,2S,5R)-2-isopropyl-5-methyl-cyclohexyl ester
  参考文献：
  名称：

  一种丙酮酸薄荷酯凉味剂及其制备方法

  摘要：

  本发明属于有机合成领域，具体公开了一种丙酮酸薄荷酯凉味剂，此外，本发明还提供了一种所述的丙酮酸薄荷酯凉味剂的制备方法，由乳酸薄荷酯与氧化剂在催化剂催作用下氧化得到；所述的催化剂为硫酸亚铁、杂多酸、溴化钠、液溴、氯气、次氯酸钠、金属负载活性炭中的至少一种。乳酸薄荷酯的转化率和丙酮酸薄荷酯的选择性均达到了99％以上。本发明丙酮酸薄荷酯作为一种凉味剂，其清凉效果持久、柔和、不刺激皮肤、无气味，使用方便容易添加；制备方法工艺简单，原料转化率高，绿色环保。

  公开号：

  CN108503548B

文献信息

• PRECURSOR COMPOUNDS OF SWEET TASTE RECEPTOR ANTAGONISTS FOR THE PREVENTION OR TREATMENT OF DISEASE
  申请人：Ley Jakob Peter

  公开号：US20110045069A1

  公开（公告）日：2011-02-24

  A description is given of precursor compounds of sweet taste receptor antagonists for the prevention or treatment of disease, in particular for the prevention or treatment of Type 2 diabetes. A description is also given of uses of these precursor compounds and edible compositions, preparations for nutrition or pleasure or semi-finished products and pharmaceutical preparations, containing such precursor compounds.

  描述了甜味受体拮抗剂的前体化合物，用于预防或治疗疾病，特别是用于预防或治疗2型糖尿病。还描述了这些前体化合物的用途，以及包含这些前体化合物的食用组合物、营养或愉悦制剂、半成品和含有这些前体化合物的药物制剂。
• Composition of Menthyl Lactate and a Mixture of Menthol Isomers
  申请人：Langner Roland

  公开号：US20080085247A1

  公开（公告）日：2008-04-10

  Described is a composition (i) comprising or (ii) essentially consisting of or (iii) consisting of (a) methyl lactate, (b) neomenthol, and (c) menthol, and optionally (d) neoisomenthol and/or (e) isomenthol, wherein said composition has a solidification point below +5° C.

  描述的是一种组合物(i)包括或(ii)基本上仅包括或(iii)由(a)乳酸甲酯，(b)新薄荷醇和(c)薄荷醇组成，可选地包括(d)新异薄荷醇和/或(e)异薄荷醇，其中所述组合物的凝固点低于+5°C。
• Photochemical Deoxygenative Hydroalkylation of Unactivated Alkenes Promoted by a Nucleophilic Organocatalyst
  作者：Jadab Majhi、Bianca Matsuo、Hyunjung Oh、Saegun Kim、Mohammed Sharique、Gary A. Molander

  DOI：10.1002/anie.202317190

  日期：2024.2.5

  A new photochemical method for deoxygenative hydroalkylation of a wide range of alkenes and lactic acid derivatives is reported. This approach utilizes thiophenol as a nucleophilic organic catalyst which forms the key intermediate of this transformation via an SN2 process.

  报道了一种用于多种烯烃和乳酸衍生物脱氧加氢烷基化的新光化学方法。该方法利用苯硫酚作为亲核有机催化剂，通过 S N 2 过程形成该转化的关键中间体。
• Process for producing cosmetic and pharmaceutical formulations, and products comprising same
  申请人：Dragoco Gerberding & Co Aktiengesellschaft

  公开号：EP0974332A1

  公开（公告）日：2000-01-26

  Cosmetic or pharmaceutical formulations such as (a) anhydrous cosmetic stick formulations and (b) anhydrous aerosol spray formulations, comprising an organic dispersion medium having particles dispersed therein, which particles are preferably prepared by a process comprising spray-drying a mixture of liposome encapsulated active agent, modified starch, and optionally a hydrocolloid gum such as maltodextrin.

  化妆品或药物制剂，如 (a) 无水化妆品棒制剂和 (b) 无水气溶胶喷雾制剂，包括一种有机分散介质，其中分散有微粒，微粒最好是通过喷雾干燥脂质体包裹的活性剂、改性淀粉和可选的水胶体胶（如麦芽糊精）混合物的工艺制备而成。
• Process for the manufacture of a spray dried powder
  申请人：Takasago International Corporation

  公开号：EP1767613A1

  公开（公告）日：2007-03-28

  The present invention relates to a process for the manufacture of a spray dried powder which comprises the the steps of (a) forming a warm, stirred aqueous slurry comprising: inorganic salts, at least one binding agent and from 0.001 to 20% by weight of capsules, based on the weight of spray dried powder, containing benefit agents including at least perfume, (b) spray drying the resultant slurry to form a spray dried powder, said capsules being such that : 1) more than 40% of the benefit agents remain encapsulated 60 minutes after dispersion thereof at 70°C in the slurry as defined in the "slurry survival test" in a sealed vessel without agitation ; 2) more than 30% of the benefit agents added for 15 minutes to an ambient slurry as defined in the "spray dry test" survive spray drying through a laboratory scale spray drier. Application : manufacture of detergents.

  本发明涉及一种制造喷雾干燥粉末的工艺，该工艺包括以下步骤：(a)形成一种温热的、搅拌的水性浆液，该浆液包括：无机盐、至少一种结合剂和按喷雾干燥粉末重量计0.001-20%（重量）的胶囊，胶囊中含有至少包括香水在内的功效剂；(b)喷雾干燥所得浆液以形成喷雾干燥粉末，所述胶囊应满足以下条件： 1) 在无搅拌的密封容器中，按照 "浆液存活试验 "的定义，在 70°C 的浆液中分散 60 分钟后，仍有 40% 以上的益肤剂被包裹； 2) 在 "喷雾干燥试验 "中定义的环境浆料中添加 15 分钟后，30% 以上的增效剂能在实验室规模的喷雾干燥机中经受住喷雾干燥。 应用：生产洗涤剂。