cis-6-Hexadecenoic Acid
(Synonyms: C16:1(6Z), C16:1Δ6, C16:1ω10, Sapienic Acid) 目录号 : GC40305A monounsaturated fatty acid
Cas No.:17004-51-2
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >99.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
cis-6-Hexadecenoic acid is a monounsaturated fatty acid and is one of the primary fatty acids in human skin. cis-6-Hexadecenoic acid levels are increased in isolated sebum from the face and back of patients with acne. In contrast, levels are decreased in the non-lesional skin and isolated sebum of atopic dermatitis patients, which correlates with an increase in S. aureus in the sebum. It is active against S. aureus in vitro when used at a concentration of 5 µg/ml at pH 5.5. cis-6-Hexadecenoic acid disrupts membrane integrity, the proton motive force, increases membrane fluidity, and inhibits the electron transport chain in S. aureus.
| Cas No. | 17004-51-2 | SDF | |
| 别名 | C16:1(6Z), C16:1Δ6, C16:1ω10, Sapienic Acid | ||
| 化学名 | 6Z-hexadecenoic acid | ||
| Canonical SMILES | CCCCCCCCC/C=C\CCCCC(O)=O | ||
| 分子式 | C16H30O2 | 分子量 | 254.1 |
| 溶解度 | Chloroform: soluble,Ethanol: soluble,Ether: soluble,Methanol: soluble | 储存条件 | Store at -20°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 3.9355 mL | 19.6773 mL | 39.3546 mL |
| 5 mM | 0.7871 mL | 3.9355 mL | 7.8709 mL |
| 10 mM | 0.3935 mL | 1.9677 mL | 3.9355 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Hyperproduction of sebaceous cis-6-Hexadecenoic Acid by esterase-reduced mutant of Rhodococcus sp. strain
J Biosci Bioeng 2007 Oct;104(4):300-3.PMID:18023803DOI:10.1263/jbb.104.300.
cis-6-Hexadecenoic Acid is a major component of human sebaceous lipids that is involved in skin self-sterilization and atopic dermatitis amelioration. It can be prepared by hydrolysis of isopropyl cis-6-hexadecenoate produced by resting cells of Rhodococcus sp. strain KSM-MT66. To devise an economical industrial-scale process for the production of this rare fatty acid, we optimized the conditions for growing rhodococcal cells. Mg(2+) and Fe(2+) ions are essential for the efficient production of isopropyl cis-6-hexadecenoate. To further increase the production of isopropyl cis-6-hexadecenoate, we created a mutant strain (T64) with reduced esterase activity by random mutagenesis using UV irradiation of MT66. Under an optimized condition, the mutant T64 produced more than 60 g l(-1) isopropyl cis-6-hexadecenoate in a 4-d cultivation, corresponding to about 52 g l(-1)cis-6-hexadecenoate.
Occurrence ofCis-6-hexadecenoic acid as the major component ofThunbergia alata seed oil
Lipids 1971 Oct;6(10):712-4.PMID:27519205DOI:10.1007/BF02531295.
An unusual series of monoenoic fatty acids constitutes about 85% of the total acids in seed oil fromThunbergia alata. The major component in the oil,cis-6-Hexadecenoic Acid (82%), is accompanied by the homologous 4-tetradecenoic (ca. 0.2%) and 8-octadecenoic (1.8%) acids. Another homologous series is represented by 5-tetradecenoic (ca. 0.2%), 7-hexadecenoic (1.8%) and the familiar 9-octadecenoic (4.4%) acids. Traces (<0.1%) of three other acids, 6-tetradecenoic and 10- and 11-octadecenoic, are also present along with palmitic (5.8%), stearic (0.6%) and linoleic (2.2%) acids. Some of the monoenoic acids have not previously been known to occur in seed oils.
Bactericidal activity of the human skin fatty acid cis-6-hexadecanoic acid on Staphylococcus aureus
Antimicrob Agents Chemother 2014 Jul;58(7):3599-609.PMID:24709265DOI:10.1128/AAC.01043-13.
Human skin fatty acids are a potent aspect of our innate defenses, giving surface protection against potentially invasive organisms. They provide an important parameter in determining the ecology of the skin microflora, and alterations can lead to increased colonization by pathogens such as Staphylococcus aureus. Harnessing skin fatty acids may also give a new avenue of exploration in the generation of control measures against drug-resistant organisms. Despite their importance, the mechanism(s) whereby skin fatty acids kill bacteria has remained largely elusive. Here, we describe an analysis of the bactericidal effects of the major human skin fatty acid cis-6-Hexadecenoic Acid (C6H) on the human commensal and pathogen S. aureus. Several C6H concentration-dependent mechanisms were found. At high concentrations, C6H swiftly kills cells associated with a general loss of membrane integrity. However, C6H still kills at lower concentrations, acting through disruption of the proton motive force, an increase in membrane fluidity, and its effects on electron transfer. The design of analogues with altered bactericidal effects has begun to determine the structural constraints on activity and paves the way for the rational design of new antistaphylococcal agents.
Host- and microbe determinants that may influence the success of S. aureus colonization
Front Cell Infect Microbiol 2012 May 4;2:56.PMID:22919647DOI:10.3389/fcimb.2012.00056.
Staphylococcus aureus may cause serious skin and soft tissue infections, deep abscesses, endocarditis, osteomyelitis, pneumonia, and sepsis. S. aureus persistently colonizes 25-30% of the adult human population, and S. aureus carriers have an increased risk for infections caused by the bacterium. The major site of colonization is the nose, i.e., the vestibulum nasi, which is covered with ordinary skin and hair follicles. Several host and microbe determinants are assumed to be associated with colonization. These include the presence and expression level of bacterial adhesins, which can adhere to various proteins in the extracellular matrix or on the cellular surface of human skin. The host expresses several antimicrobial peptides and lipids. The level of β-defensin 3, free sphingosine, and cis-6-Hexadecenoic Acid are found to be associated with nasal carriage of S. aureus. Other host factors are certain polymorphisms in Toll-like receptor 2, mannose-binding lectin, C-reactive protein, glucocorticoid-, and vitamin D receptor. Additional putative determinants for carriage include genetic variation and expression of microbial surface components recognizing adhesive matrix molecules and their interaction partners, as well as variation among humans in the ability of recognizing and responding appropriately to the bacteria. Moreover, the available microflora may influence the success of S. aureus colonization. In conclusion, colonization is a complex interplay between the bacteria and its host. Several bacterial and host factors are involved, and an increased molecular understanding of these are needed.
Deficient production of hexadecenoic acid in the skin is associated in part with the vulnerability of atopic dermatitis patients to colonization by Staphylococcus aureus
Dermatology 2005;211(3):240-8.PMID:16205069DOI:10.1159/000087018.
Background and objectives: As one of the major skin fatty acids, cis-6-Hexadecenoic Acid (C16:1Delta6) exhibits a specific antibacterial activity and might play a specific role in the defense mechanism against Staphylococcus aureus, in healthy subjects whereas S. aureus frequently colonizes the skin of patients with atopic dermatitis (AD). Methods: Fatty acid composition of sebum at the recovery level was analyzed by gas chromatography and S. aureus colonizing the skin was assessed by the 'cup-scrub' method (9 patients and 10 healthy controls). To evaluate in vivo effect of C16:1Delta6 on colonization, C16:1Delta6 was applied for 2 weeks on the upper arm skin of another group of AD patients (11 patients). Results: Analysis of sebum lipids revealed that there is a significant lower free C16:1Delta6 content in nonlesional skin from AD patients compared with healthy controls. This lower content is also accompanied by a significantly lower level of C16:1Delta6 in the total fatty acid composition of sebum (analyzed following hydrolysis). The lower level of free C16:1Delta6 correlated significantly (R(2) = 0.41, p < 0.01) with the numbers of S. aureus colonizing nonlesional skin. Topical application of free C16:1Delta6 on the skin of AD patients for 2 weeks abolished the markedly increased bacterial count in 6 out of the 8 AD patients tested. Conclusions: Free C16:1Delta6 may be involved in the defense mechanism against S. aureus in healthy skin and this deficit triggers the susceptibility of the skin to colonization by S. aureus in AD.