菜豆苷 | 554-35-8

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: 菜豆苷
• 中文别名: 亚麻苷；亞麻苷
• 英文名称: linamarin
• 英文别名: 2-((β-D-glucopyranosyl)oxy)-2-methylpropane nitrile；1-Cyano-1-methylethyl-β-D-glucopyranoside；2-(β-D-glucopyranosyloxy)-2-methyl-propanenitrile；2-methyl-2-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxypropanenitrile
• CAS: 554-35-8
• 化学式: C₁₀H₁₇NO₆
• mdl: MFCD00036209
• 分子量: 247.248
• InChiKey: QLTCHMYAEJEXBT-ZEBDFXRSSA-N

物化性质

• 熔点：
  142-143°C
• 比旋光度：
  D18 -29°
• 沸点：
  390.28°C (rough estimate)
• 密度：
  1.2868 (rough estimate)
• 溶解度：
  溶于DMSO、甲醇和乙醇
• 物理描述：
  Solid
• 颜色/状态：
  NEEDLES
• 味道：
  BITTER
• 旋光度：
  SPECIFIC OPTICAL ROTATION: -29 DEG @ 18 °C/D
• 碰撞截面：
  157.3 Ų [M+Na]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]

计算性质

• 辛醇/水分配系数(LogP)：
  -1.8
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  123
• 氢给体数：
  4
• 氢受体数：
  7

ADMET

代谢

亚麻幼苗通过UDP-葡萄糖依赖的酮腈水合酶将放射性缬氨酸或丙酮腈水合酶生物合成氰马林，亚麻种子预培养亮氨酸，抑制氰马林生物合成，亮氨酸是洛托甾醇的前体。

THE BIOSYNTHESIS OF LINAMARIN FROM RADIOACTIVE VALINE OR ACETONE CYANOHYDRIN BY UDP-GLUCOSE-DEPENDENT KETONE CYANOHYDRIN GLUCOSYLTRANSFERASE IN FLAX SEEDLINGS WAS INHIBITED BY PREINCUBATION OF FLAX SEEDLINGS WITH ISOLEUCINE, THE PRECURSOR OF LOTAUSTRALIN.

来源:Hazardous Substances Data Bank (HSDB)

代谢

接触到人体肠道中的酶和肠道菌群后，亚麻氰可以分解为有毒的化学物质氢氰酸。这是通过细胞壁中发现的亚麻氰酶来实现的。咀嚼植物使酶接触到亚麻氰，将其转化为丙酮氰醇，然后自发分解为氢氰酸。摄入和吸收的亚麻氰会迅速通过尿液排出，而糖苷本身似乎不具有急性毒性。（L630）有机腈通过肝脏中的细胞色素P450酶的作用转化为氰离子。氰化物迅速被吸收并在全身分布。氰化物主要通过罗丹酶或3-巯基丙酮酸硫转移酶代谢为硫氰酸盐。氰化物代谢物通过尿液排出。（L96）

Upon exposure to enzymes and gut flora in the human intestine, linamarin can decompose to the toxic chemical hydrogen cyanide. This occurs via the enzyme linamarase, which is found in the cell wall of the plant. Chewing of the plant allows the enzyme to contact the linamarin, converting it into acetone cyanohydrin, which then spontaneously decomposes to hydrogen cyanide. Ingested and absorbed linamarin is rapidly excreted in the urine and the glucoside itself does not appear to be acutely toxic. (L630) Organic nitriles are converted into cyanide ions through the action of cytochrome P450 enzymes in the liver. Cyanide is rapidly absorbed and distributed throughout the body. Cyanide is mainly metabolized into thiocyanate by either rhodanese or 3-mercaptopyruvate sulfur transferase. Cyanide metabolites are excreted in the urine. (L96)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 毒性总结

有机腈在体内和体外均可分解成氰化物离子。因此，有机腈的主要毒性机制是它们产生有毒的氰化物离子或氢氰酸。氰化物是电子传递链第四个复合体（存在于真核细胞线粒体膜中）中的细胞色素c氧化酶的抑制剂。它与这种酶中的三价铁原子形成配合物。氰化物与这种细胞色素的结合阻止了电子从细胞色素c氧化酶传递到氧气。结果，电子传递链被中断，细胞无法再通过有氧呼吸产生ATP能量。主要依赖有氧呼吸的组织，如中枢神经系统和心脏，受到特别影响。氰化物也通过与过氧化氢酶、谷胱甘肽过氧化物酶、变性血红蛋白、羟钴胺素、磷酸酶、酪氨酸酶、抗坏血酸氧化酶、黄嘌呤氧化酶、琥珀酸脱氢酶以及Cu/Zn超氧化物歧化酶结合，产生一些毒性效应。氰化物与变性血红蛋白中的三价铁离子结合，形成无活性的氰化变性血红蛋白。

Organic nitriles decompose into cyanide ions both in vivo and in vitro. Consequently the primary mechanism of toxicity for organic nitriles is their production of toxic cyanide ions or hydrogen cyanide. Cyanide is an inhibitor of cytochrome c oxidase in the fourth complex of the electron transport chain (found in the membrane of the mitochondria of eukaryotic cells). It complexes with the ferric iron atom in this enzyme. The binding of cyanide to this cytochrome prevents transport of electrons from cytochrome c oxidase to oxygen. As a result, the electron transport chain is disrupted and the cell can no longer aerobically produce ATP for energy. Tissues that mainly depend on aerobic respiration, such as the central nervous system and the heart, are particularly affected. Cyanide is also known produce some of its toxic effects by binding to catalase, glutathione peroxidase, methemoglobin, hydroxocobalamin, phosphatase, tyrosinase, ascorbic acid oxidase, xanthine oxidase, succinic dehydrogenase, and Cu/Zn superoxide dismutase. Cyanide binds to the ferric ion of methemoglobin to form inactive cyanmethemoglobin. (L97)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 致癌物分类

对人类无致癌性（未列入国际癌症研究机构IARC清单）。

No indication of carcinogenicity to humans (not listed by IARC).

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 健康影响

食用由高亚麻苦苷含量、加工不足的木薯根制成的食物与饮食中毒有关，尤其是在非洲人群中被称为肯佐的上运动神经元疾病。饮食中暴露于亚麻苦苷也被报道为发展葡萄糖不耐症和糖尿病的风险因素。

Ingestion of food prepared from insufficiently processed cassava roots with high linamarin levels has been associated with dietary toxicity, particularly with the upper motor neuron disease known as konzo to the African populations. Dietary exposure to linamarin has also been reported as a risk factor in developing glucose intolerance and diabetes. (L630)

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 暴露途径

口腔

Oral

来源:Toxin and Toxin Target Database (T3DB)

毒理性

• 症状

氰化物中毒的表现包括快速、深大的呼吸和呼吸急促，全身无力，眩晕，头痛，头晕，混乱，抽搐/癫痫发作，最终失去意识。

Cyanide poisoning is identified by rapid, deep breathing and shortness of breath, general weakness, giddiness, headaches, vertigo, confusion, convulsions/seizures and eventually loss of consciousness. (L96, L97)

来源:Toxin and Toxin Target Database (T3DB)

吸收、分配和排泄

威斯塔大鼠体重约100克，通过胃管给予30毫克纯木薯氰苷（木薯中的一种主要生氰糖苷）。在大鼠的粪便或血液中未检测到完整的木薯氰苷，但在尿液中排出了5.65毫克的木薯氰苷，同时还有0.823毫克的硫氰离子。

WISTAR RATS, ABOUT 100 G IN WEIGHT, WERE DOSED BY STOMACH TUBE WITH 30 MG OF PURE LINAMARIN (A MAJOR CYANOGENIC GLUCOSIDE IN CASSAVA). NO INTACT LINAMARIN WAS IDENTIFIED IN THE FECES OR BLOOD BUT 5.65 MG WAS EXCRETED IN THE URINE ALONG WITH 0.823 MG OF THIOCYANATE ION.

来源:Hazardous Substances Data Bank (HSDB)

吸收、分配和排泄

40名孕妇的羊水和血液样本被分析以测定其中的硫氰酸盐含量。羊水中的浓度范围在0.66-3.88毫摩尔/升，而血液样本的浓度范围在0.70-2.80毫摩尔/升。浓度最高的出现在那些食用大量加里（木薯布丁）的下层阶级，加里是一种含有氰糖苷亚麻苦甙的主食。解毒产物硫氰酸盐似乎能透过胎盘屏障。文中讨论了这一现象在甲状腺肿和克汀病病因学中的意义。

THE AMNIOTIC FLUIDS AND BLOOD SAMPLES OF 40 PREGNANT WOMEN WERE ANALYZED FOR THIOCYANATE. THE CONCENTRATION IN THE AMNIOTIC FLUIDS VARIED FROM 0.66-3.88 MMOL/L WHILE THOSE OF THE BLOOD SAMPLES VARIED FROM 0.70-2.80 MMOL/L. THE HIGHEST CONCENTRATIONS OCCURRED IN THE LOWER CLASS WHO EAT A LOT OF GARI (CASSAVA PUDDING), WHICH IS THE STAPLE DIET THAT CONTAINS THE CYANOGENIC GLYCOSIDE LINAMARIN. THE DETOXIFICATION PRODUCT, THIOCYANATE, SEEMS TO PENETRATE THE PLACENTAL BARRIER. THE IMPLICATION OF THIS IN THE ETIOLOGY OF GOITER AND CRETINISM WAS DISCUSSED.

来源:Hazardous Substances Data Bank (HSDB)

安全信息

• 危险品标志：
  Xn
• 危险类别码：
  R20/22,R36/37/38

SDS

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SECTION 1: Identification of the substance/mixture and of the company/undertaking
Product identifiers
: α-Hydroxyisobutyronitrile β-D-glucopyranoside
Product name
REACH No. : A registration number is not available for this substance as the substance
or its uses are exempted from registration, the annual tonnage does not
require a registration or the registration is envisaged for a later
registration deadline.
CAS-No. : 554-35-8
Relevant identified uses of the substance or mixture and uses advised against
Identified uses : Laboratory chemicals, Manufacture of substances

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SECTION 2: Hazards identification
Classification of the substance or mixture
Classification according to Regulation (EC) No 1272/2008
Acute toxicity, Inhalation (Category 4), H332
Acute toxicity, Oral (Category 4), H302
Skin irritation (Category 2), H315
Eye irritation (Category 2), H319
Specific target organ toxicity - single exposure (Category 3), H335
For the full text of the H-Statements mentioned in this Section, see Section 16.
Classification according to EU Directives 67/548/EEC or 1999/45/EC
Xn Harmful R20/22, R36/37/38
For the full text of the R-phrases mentioned in this Section, see Section 16.
Label elements
Labelling according Regulation (EC) No 1272/2008
Pictogram
Signal word Warning
Hazard statement(s)
H302 Harmful if swallowed.
H315 Causes skin irritation.
H319 Causes serious eye irritation.
H332 Harmful if inhaled.
H335 May cause respiratory irritation.
Precautionary statement(s)
P261 Avoid breathing dust/ fume/ gas/ mist/ vapours/ spray.
P305 + P351 + P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove
contact lenses, if present and easy to do. Continue rinsing.
Supplemental Hazard none
Statements
Other hazards - none

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SECTION 3: Composition/information on ingredients
Substances
Chemical characterization : Natural product
: α-Hydroxyisobutyronitrile β-D-glucose
Synonyms
2-(β-D-Glucopyranosyloxy)-2-methylpropionitrile
Linamarin
Formula : C10H17NO6
Molecular Weight : 247,25 g/mol
CAS-No. : 554-35-8
Hazardous ingredients according to Regulation (EC) No 1272/2008
Component Classification Concentration
Linamarin
CAS-No. 554-35-8 Acute Tox. 4; Skin Irrit. 2; Eye <= 100 %
Irrit. 2; STOT SE 3; H302,
H315, H319, H332, H335
Hazardous ingredients according to Directive 1999/45/EC
Component Classification Concentration
Linamarin
CAS-No. 554-35-8 Xn, R20/22 - R36/37/38 <= 100 %
For the full text of the H-Statements and R-Phrases mentioned in this Section, see Section 16

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SECTION 4: First aid measures
Description of first aid measures
General advice
Consult a physician. Show this safety data sheet to the doctor in attendance.
If inhaled
If breathed in, move person into fresh air. If not breathing, give artificial respiration. Consult a physician.
In case of skin contact
Wash off with soap and plenty of water. Consult a physician.
In case of eye contact
Rinse thoroughly with plenty of water for at least 15 minutes and consult a physician.
If swallowed
Never give anything by mouth to an unconscious person. Rinse mouth with water. Consult a physician.
Most important symptoms and effects, both acute and delayed
The most important known symptoms and effects are described in the labelling (see section 2.2) and/or in
section 11
Indication of any immediate medical attention and special treatment needed
no data available

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SECTION 5: Firefighting measures
Extinguishing media
Suitable extinguishing media
Use water spray, alcohol-resistant foam, dry chemical or carbon dioxide.
Special hazards arising from the substance or mixture
Carbon oxides, nitrogen oxides (NOx)
Advice for firefighters
Wear self contained breathing apparatus for fire fighting if necessary.
Further information
no data available

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SECTION 6: Accidental release measures
Personal precautions, protective equipment and emergency procedures
Use personal protective equipment. Avoid dust formation. Avoid breathing vapours, mist or gas. Ensure
adequate ventilation. Evacuate personnel to safe areas. Avoid breathing dust.
For personal protection see section 8.
Environmental precautions
Do not let product enter drains.
Methods and materials for containment and cleaning up
Pick up and arrange disposal without creating dust. Sweep up and shovel. Keep in suitable, closed
containers for disposal.
Reference to other sections
For disposal see section 13.

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SECTION 7: Handling and storage
Precautions for safe handling
Avoid contact with skin and eyes. Avoid formation of dust and aerosols.
Provide appropriate exhaust ventilation at places where dust is formed.
For precautions see section 2.2.
Conditions for safe storage, including any incompatibilities
Store in cool place. Keep container tightly closed in a dry and well-ventilated place.
Specific end use(s)
A part from the uses mentioned in section 1.2 no other specific uses are stipulated

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SECTION 8: Exposure controls/personal protection
Control parameters
Components with workplace control parameters
Exposure controls
Appropriate engineering controls
Handle in accordance with good industrial hygiene and safety practice. Wash hands before breaks and
at the end of workday.
Personal protective equipment
Eye/face protection
Safety glasses with side-shields conforming to EN166 Use equipment for eye protection tested
and approved under appropriate government standards such as NIOSH (US) or EN 166(EU).
Skin protection
Handle with gloves. Gloves must be inspected prior to use. Use proper glove removal technique
(without touching glove's outer surface) to avoid skin contact with this product. Dispose of
contaminated gloves after use in accordance with applicable laws and good laboratory practices.
Wash and dry hands.
The selected protective gloves have to satisfy the specifications of EU Directive 89/686/EEC and
the standard EN 374 derived from it.
Full contact
Material: Nitrile rubber
Minimum layer thickness: 0,11 mm
Break through time: 480 min
Material tested:Dermatril® (KCL 740 / Z677272, Size M)
Splash contact
Material: Nitrile rubber
Minimum layer thickness: 0,11 mm
Break through time: 480 min
Material tested:Dermatril® (KCL 740 / Z677272, Size M)
data source: KCL GmbH, D-36124 Eichenzell, phone [phone], test method: EN374
If used in solution, or mixed with other substances, and under conditions which differ from EN 374,
contact the supplier of the CE approved gloves. This recommendation is advisory only and must
be evaluated by an industrial hygienist and safety officer familiar with the specific situation of
anticipated use by our customers. It should not be construed as offering an approval for any
specific use scenario.
Body Protection
Complete suit protecting against chemicals, The type of protective equipment must be selected
according to the concentration and amount of the dangerous substance at the specific workplace.
Respiratory protection
For nuisance exposures use type P95 (US) or type P1 (EU EN 143) particle respirator.For higher
level protection use type OV/AG/P99 (US) or type ABEK-P2 (EU EN 143) respirator cartridges.
Use respirators and components tested and approved under appropriate government standards
such as NIOSH (US) or CEN (EU).
Control of environmental exposure
Do not let product enter drains.

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SECTION 9: Physical and chemical properties
Information on basic physical and chemical properties
a) Appearance Form: solid
b) Odour no data available
c) Odour Threshold no data available
d) pH no data available
e) Melting point/freezing no data available
point
f) Initial boiling point and no data available
boiling range
g) Flash point no data available
h) Evapouration rate no data available
i) Flammability (solid, gas) no data available
j) Upper/lower no data available
flammability or
explosive limits
k) Vapour pressure no data available
l) Vapour density no data available
m) Relative density no data available
n) Water solubility no data available
o) Partition coefficient: n- no data available
octanol/water
p) Auto-ignition no data available
temperature
q) Decomposition no data available
temperature
r) Viscosity no data available
s) Explosive properties no data available
t) Oxidizing properties no data available
Other safety information
no data available

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SECTION 10: Stability and reactivity
Reactivity
no data available
Chemical stability
Stable under recommended storage conditions.
Possibility of hazardous reactions
no data available
Conditions to avoid
no data available
Incompatible materials
Oxidizing agents
Hazardous decomposition products
Other decomposition products - no data available
In the event of fire: see section 5

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SECTION 11: Toxicological information
Information on toxicological effects
Acute toxicity
no data available
Skin corrosion/irritation
no data available
Serious eye damage/eye irritation
no data available
Respiratory or skin sensitisation
no data available
Germ cell mutagenicity
no data available
Carcinogenicity
IARC: No component of this product present at levels greater than or equal to 0.1% is identified as
probable, possible or confirmed human carcinogen by IARC.
Reproductive toxicity
Developmental Toxicity - Hamster - Oral
Specific Developmental Abnormalities: Musculoskeletal system.
Specific target organ toxicity - single exposure
Inhalation - May cause respiratory irritation.
Specific target organ toxicity - repeated exposure
no data available
Aspiration hazard
no data available
Additional Information
RTECS: TZ4850000
To the best of our knowledge, the chemical, physical, and toxicological properties have not been
thoroughly investigated.

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SECTION 12: Ecological information
Toxicity
no data available
Persistence and degradability
no data available
Bioaccumulative potential
no data available
Mobility in soil
no data available
Results of PBT and vPvB assessment
PBT/vPvB assessment not available as chemical safety assessment not required/not conducted
Other adverse effects
no data available

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SECTION 13: Disposal considerations
Waste treatment methods
Product
Offer surplus and non-recyclable solutions to a licensed disposal company. Dissolve or mix the material
with a combustible solvent and burn in a chemical incinerator equipped with an afterburner and scrubber.
Contaminated packaging
Dispose of as unused product.

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SECTION 14: Transport information
UN number
ADR/RID: - IMDG: - IATA: -
UN proper shipping name
ADR/RID: Not dangerous goods
IMDG: Not dangerous goods
IATA: Not dangerous goods
Transport hazard class(es)
ADR/RID: - IMDG: - IATA: -
Packaging group
ADR/RID: - IMDG: - IATA: -
Environmental hazards
ADR/RID: no IMDG Marine pollutant: no IATA: no
Special precautions for user
no data available

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SECTION 15 - REGULATORY INFORMATION
N/A

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SECTION 16 - ADDITIONAL INFORMATION
N/A

反应信息

• 作为反应物：
  描述：

  菜豆苷 在 水 、