1. 作为抗增殖槐糖脂的前体:
- 1-十六醇（1-Hexadecanol）（鲸蜡醇）作为脂肪酸前体，通过微生物发酵合成新型槐糖脂（C16-SL） [1]
- 衍生的C16-SL对HeLa细胞呈剂量依赖性抗增殖活性，48小时处理的IC₅₀值为125 μM；1-十六醇（1-Hexadecanol）本身在测试浓度（最高200 μM）下无直接抗增殖活性 [1]
2. C16-SL（源于1-十六醇）的凋亡诱导作用:
- 150 μM C16-SL处理24小时后，Annexin V-FITC/PI染色显示HeLa细胞凋亡率升至42.3%（对照组为2.1%） [1]
- DAPI染色显示，C16-SL处理的HeLa细胞出现染色质浓缩和核碎裂，这与前体1-十六醇（1-Hexadecanol）对槐糖脂活性的结构贡献相关 [1]
3. 细胞形态变化:
- 100 μM C16-SL处理24小时后，HeLa细胞出现皱缩、脱附及凋亡小体形成；1-十六醇（1-Hexadecanol）本身不会引发此类变化 [1]

1. HeLa细胞培养及增殖检测（针对源于1-十六醇的C16-SL）:
- HeLa细胞在含10%胎牛血清（FBS）和抗生素的DMEM培养基中培养，置于37°C、5% CO₂培养箱 [1]
- 细胞（5×10³个/孔）接种于96孔板，用C16-SL（0-200 μM，以1-十六醇（1-Hexadecanol）为前体合成）处理24-72小时；1-十六醇（1-Hexadecanol）本身（0-200 μM）作为对照 [1]
- 每孔加入MTT溶液（5 mg/ml，20 μl）孵育4小时，二甲基亚砜（DMSO）溶解甲臜结晶后，在570 nm处测吸光度，计算细胞活力及IC₅₀ [1]
2. 凋亡检测（Annexin V-FITC/PI双染法）:
- HeLa细胞（1×10⁶个/ml）用150 μM C16-SL处理24小时；1-十六醇（1-Hexadecanol）（150 μM）作为对照 [1]
- 收集细胞，PBS洗涤后，用Annexin V-FITC和PI避光染色15分钟，流式细胞仪分析凋亡率 [1]
3. DAPI染色观察核形态:
- 处理后的HeLa细胞用4%多聚甲醛固定15分钟，PBS洗涤后，用DAPI（1 μg/ml）染色10分钟 [1]
- 荧光显微镜下观察核变化（染色质浓缩、碎裂），1-十六醇（1-Hexadecanol）处理组无异常核形态 [1]

Absorption, Distribution and Excretion
Following ingestion of a 2.0 g/kg dose of cetyl alcohol in rats, partial absorption was observed. Gavage administration of 0.2 mg cetyl alcohol via gastric tube to rats showed good absorption, with 63-96% of the radiolabeled cetyl alcohol detected in lymph. Approximately 15% of the cetyl alcohol remained unchanged as it passed through the small intestinal mucosal cells, but most was oxidized to palmitic acid. The absorption rate in poultry has been reported to be 26%. Following ingestion of a 2.0 g/kg dose in rats, approximately 20% of the dose was excreted in feces in its unchanged molecular form. This is likely due to the interconversion of fatty acids and alcohols, leading to the conversion of palmitic acid to cetyl alcohol as it passes through the intestinal mucosal cells into the intestinal lumen. In rats, cetyl alcohol is also excreted in urine as conjugated glucuronic acid and exhaled carbon dioxide. Following ingestion of a 2.0 g/kg body weight dose in rats, 1-hexadecane was partially absorbed and metabolized, with approximately 20% excreted unchanged in feces.

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Metabolism/Metabolites>
In rats, cetyl alcohol is partially metabolized to palmitic acid after ingestion of a dose of 2.0 g/kg. After administration of 0.2 mg cetyl alcohol via gastric tube to rats, most of the cetyl alcohol is oxidized to palmitic acid as it passes through the small intestinal mucosal cells and is incorporated into triglycerides and phospholipids.
Cetyl alcohol is oxidized to the corresponding fatty acid, palmitic acid, in rats.
Primary fatty alcohols undergo two main reactions in vivo: oxidation to carboxylic acids and direct conjugation with glucuronic acid. The first reaction generates an intermediate aldehyde, from which the carboxylic acid may be completely oxidized to carbon dioxide, excreted as carbon dioxide, or conjugated with glucuronic acid to form ester glucuronide. The extent to which alcohols undergo the second reaction (i.e., direct conjugation with ether glucuronide) appears to depend on the rate of the first reaction; unless high doses are administered, alcohols are typically oxidized rapidly to small amounts of ether glucuronide.

Toxicity Data
LCLo (Rat) = 2,220 mg/m³/6h

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Interactions ... Chymotrypsin loses its activity within 30 minutes in the presence of triethanolamine stearate, tripalmitate, and cetyl alcohol.

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Non-human Toxicity Values LD50 Guinea Pig Dermal Administration < 10 g/kg
LD50 Rat Oral Administration 5 g/kg
LD50 Rat Intraperitoneal Administration 1600 mg/kg
LD50 Mouse Oral Administration 3200 mg/kg
LD50 Mouse Intraperitoneal Administration 1600 mg/kg

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- C16-SL (derived from 1-hexadecyl alcohol) toxicity to normal cells: C16-SL (200 μM) showed low cytotoxicity to Vero cells. (Normal African green monkey kidney cells), cell viability was 81.2% (while HeLa cells were 32.5%) [1]

[1]. Anti-proliferative effect of novel primary cetyl alcohol derived sophorolipids against human cervical cancer cells HeLa. PLoS One. 2017 Apr 18;12(4):e0174241.

[2]. Peroxisome-driven ether-linked phospholipids biosynthesis is essential for ferroptosis. Cell Death Differ. 2021 Aug;28(8):2536-2551.

Hexadecane-1-ol is a long-chain primary fatty alcohol, formed by replacing the hydroxyl group at the 1-position of hexadecane. It is a human metabolite, an algal metabolite, a plant metabolite, and a flavoring agent. It is a long-chain primary fatty alcohol and also a type of hexadecyl alcohol. Cetyl alcohol, also known as 1-hexadecyl alcohol or n-hexadecyl alcohol, is a 16-carbon fatty alcohol with the chemical formula CH3(CH2)15OH. It can be prepared by the reduction reaction of palmitic acid. Cetyl alcohol is a waxy white powder or flakes at room temperature, insoluble in water but soluble in alcohols and oils. Discovered by Chevrenl in 1913, cetyl alcohol is one of the oldest known long-chain alcohols. It may be found in cosmetics and personal care products such as shampoos, creams, and lotions. Cetyl alcohol is mainly used as a sunscreen, emulsifier, and thickener, capable of altering the consistency of liquids and enhancing and stabilizing foaming ability. Due to its water-retaining properties, cetyl alcohol is often used as a moisturizer to prevent dry and chapped skin. According to federal regulations of the U.S. Food and Drug Administration (FDA), cetyl alcohol is a safe synthetic fatty acid that can be used in the synthesis of food and food ingredients, provided that its total alcohol content is not less than 98% and its linear alcohol content is not less than 94%. Cetyl alcohol is also listed as an over-the-counter drug ingredient as a skin protectant to relieve skin irritation caused by poison ivy, poison oak, sumac, and insect bites. Cetyl alcohol has been reported to have mild skin or eye irritation. 1-Hexadecyl alcohol has been found in tea (Camellia sinensis), angelica (Angelica gigas), and other organisms with relevant data. Cetyl alcohol is a synthetic solid fatty alcohol and a nonionic surfactant. Cetyl alcohol is used as an emulsifier in pharmaceutical preparations. Cetyl alcohol, also known as 1-hexadecyl alcohol and palmitol, is a solid organic compound belonging to the alcohol class. Its chemical formula is CH3(CH2)15OH. At room temperature, cetyl alcohol is a waxy white solid or flakes. It belongs to the fatty alcohol class. With the decline of commercial whaling, cetyl alcohol is no longer primarily produced from whale oil, but rather as a final product of the petroleum industry or from vegetable oils such as palm and coconut oil. Cetyl alcohol is produced from palm oil, hence one of its alternative names is palm alcohol.
See also: cetyl alcohol; cetyl palmitate; tylosap (ingredient); moringa leaf oil (partial); C14-18 alcohol (note moved to)...see more...

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Drug Indications
No drug indications. Can be used as an indirect additive to food contact substances, or as a commercial or cosmetic ingredient.

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Mechanism of Action
Cetyl alcohol has moisturizing properties, making it a suitable emulsifier and stabilizer in pharmaceutical preparations. It is also present in washable ointment bases due to its dispersibility and stability. The potential antibacterial activity of cetyl alcohol may result from altered cell membrane permeability, which hinders the absorption of essential nutrients and induces the outward diffusion of important cellular components. The proposed mechanism of action is thought to be similar to other long-chain fatty alcohols with the same antibacterial activity, such as myristol and behenol.

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Therapeutic Uses
Synthetic surfactants (Exosurf) and their non-surfactant components, tylosaprol and cetyl alcohol, can act as antioxidants; in vivo infusion has been associated with a reduction in hyperoxia-induced injury in rats.

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Pharmacodynamics
Cetyl alcohol has a dermal protective effect, combating skin irritation caused by bites, rashes, and stings. Cetyl alcohol has been reported to inhibit the growth of Mycoplasma gallisepticum and Mycoplasma pneumoniae.

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1. Chemical background of 1-hexadecyl alcohol:
-1-hexadecyl alcohol (cetyl alcohol) is a saturated fatty alcohol containing 16 carbon atoms, and is commonly used as a precursor for the synthesis of lipids and surfactants[1]
2. Synthesis of C16-SL using 1-hexadecyl alcohol:
-1-hexadecyl alcohol was added as a carbon source to a microbial culture (Candida bombicola), and fermented at 30°C for 120 hours. The resulting sophorolipid (C16-SL) was purified by solvent extraction and column chromatography[1]
3. Mechanism of action of C16-SL (derived from 1-hexadecyl alcohol):
-C16-SL may induce apoptosis in HeLa cells by disrupting the cell membrane and activating apoptosis signaling pathways;
1-hexadecyl alcohol itself does not trigger such a mechanism[1]

C16H34O

242.4406

242.26

36653-82-4

1-Hexadecanol-d5;1219799-18-4;1-Hexadecanol-d4;1398065-49-0;1-Hexadecanol-d31;203633-15-2;1-Hexadecanol-d33;284474-73-3;1-Hexadecanol-d3;75736-52-6

2682

White to off-white solid powder

0.8±0.1 g/cm3

310.9±5.0 °C at 760 mmHg

49-51 °C

135.0±0.0 °C

0.0±1.5 mmHg at 25°C

1.448

7.25

20.23

1

1

14

17

123

0

BXWNKGSJHAJOGX-UHFFFAOYSA-N

InChI=1S/C16H34O/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17/h17H,2-16H2,1H3

hexadecan-1-ol

2934.99.9001

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

注意： 本产品在运输和储存过程中需避光。

Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

DMSO : ~10 mg/mL (~41.25 mM)

配方 1 中的溶解度: 1 mg/mL (4.12 mM) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (这些助溶剂从左到右依次添加，逐一添加), 悬浮液；超声助溶。
例如，若需制备1 mL的工作液，可将100 μL 10.0 mg/mL澄清DMSO储备液加入400 μL PEG300中，混匀；然后向上述溶液中加入50 μL Tween-80，混匀；加入450 μL生理盐水定容至1 mL。
*生理盐水的制备：将 0.9 g 氯化钠溶解在 100 mL ddH₂O中，得到澄清溶液。

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配方 2 中的溶解度: ≥ 1 mg/mL (4.12 mM) (饱和度未知) in 10% DMSO + 90% Corn Oil (这些助溶剂从左到右依次添加，逐一添加), 澄清溶液。
例如，若需制备1 mL的工作液，可将 100 μL 10.0 mg/mL 澄清 DMSO 储备液加入到 900 μL 玉米油中并混合均匀。

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请根据您的实验动物和给药方式选择适当的溶解配方/方案：
1、请先配制澄清的储备液(如：用DMSO配置50 或 100 mg/mL母液(储备液));
2、取适量母液，按从左到右的顺序依次添加助溶剂，澄清后再加入下一助溶剂。以 下列配方为例说明 (注意此配方只用于说明，并不一定代表此产品 的实际溶解配方):
10% DMSO → 40% PEG300 → 5% Tween-80 → 45% ddH2O (或 saline);
假设最终工作液的体积为 1 mL, 浓度为5 mg/mL: 取 100 μL 50 mg/mL 的澄清 DMSO 储备液加到 400 μL PEG300 中，混合均匀/澄清；向上述体系中加入50 μL Tween-80，混合均匀/澄清；然后继续加入450 μL ddH2O (或 saline)定容至 1 mL；
3、溶剂前显示的百分比是指该溶剂在最终溶液/工作液中的体积所占比例;
4、 如产品在配制过程中出现沉淀/析出，可通过加热(≤50℃)或超声的方式助溶;
5、为保证最佳实验结果，工作液请现配现用！
6、如不确定怎么将母液配置成体内动物实验的工作液，请查看说明书或联系我们;
7、 以上所有助溶剂都可在 Invivochem.cn网站购买。