Organic nomenclature in Chinese

The Chinese Chemical Society[1] (CCS; simplified Chinese: 中国化学会; traditional Chinese: 中國化學會) lays out a set of rules based on those given by the International Union of Pure and Applied Chemistry (IUPAC) for the purpose of systematic organic nomenclature in Chinese. The chemical names derived from these rules are meant to correspond with the English IUPAC name in a manner that is close to one-to-one, while being adapted to and taking advantage of the logographic nature of the Chinese written language. A standard set of characters invented during the 20th century (vide infra), along with characters for the chemical elements and characters corresponding to standard chemical prefixes and suffixes, are used for this purpose.

Derivation of Chinese characters

The majority of the Chinese characters used for this purpose are phonosemantic compounds, with part of the character giving a general semantic category and the other part providing a pronunciation, usually based on the international (European) pronunciation. There are four common radicals (the part of the character that gives the semantic category) for these characters:

  • 火 (huǒ, fire) e.g.: 烷 (wán, alkane), common for hydrocarbons
  • 酉 (yǒu, ritual wine vessel) e.g.: 酮 (tóng, ketone), common for oxygenated functionalities
  • 艸 (cǎo, grass) e.g. 苯 (běn, benzene, phenyl), common for aromatic compounds and terpenes
  • 肉 (ròu, meat, flesh) e.g. 腙 (zōng, hydrazone), common for nitrogen-containing functionalities

Additionally, the mouth radical (口, kǒu) is affixed to characters that are used for their sound only. This occurs often in the transliteration of the names of heterocyclic compounds, (e.g., 吡啶, "bǐdìng", pyridine). These characters are also used for the transliteration of non-chemical terms from foreign languages.

Table

Below is a table, in pinyin order, of the Chinese names of major organic compounds, radicals, and functional groups. Characters given are in traditional Chinese, followed by simplified Chinese where possible. Since the characters are modern creations, the traditional Chinese characters are analogous (with traditional components in place of simplified components). The Mandarin pronunciation of each character, as said in Mainland China, is in pronunciation column. Any Taiwanese pronunciations that differ from the Mainland Chinese pronunciations are put in the notes. Other usages of characters are etymologically unrelated to the character's meaning as names for organic compounds, radicals, and functional groups unless otherwise stated. This list is not exhaustive, although many of the other characters used for this purpose can only be found in specialist dictionaries.

Chinese names of organic compounds, radicals, and functional groups
CharacterPhoneticPronunciationOrigin/Notes
amineān 'peace'ànFrom ammonia, 氨 ān, itself based on the European pronunciation (銨/铵 ǎn 'ammonia', with the metal radical is used for ammonium salts). Pronounced as ān in Taiwan. This character is also pronounced è (ān in Taiwan) to mean 'to putrefy (for meat)'.
azuleneào 'mysterious'àoEuropean pronunciation. This character is also pronounced , meaning 'wild grapes'.
benzene or phenylběn 'this','root'běnEuropean pronunciation. This character is also used to mean 'the appearance of grass growing'.
吡啶 pyridine 'compare' and 定 dìng 'stability'bǐdìngTransliteration. 吡 is also used to mean 'slander' or 'compare'; when it is pronounced , it is bird onomatopoeia.
吡咯 pyrrole 'compare' and 各 'each'bǐluòTransliteration. See note for 吡啶 for other usages for 吡. 咯 is also pronounced or , meaning 'cackle', 'cluck', 'this', or 'pickled mustard'; it is also pronounced (luò in Taiwan), meaning 'to cough up'; it is also pronounced lo, used as an end particle.
benzylbiàn 'hurried'biànEuropean pronunciation
卟吩 porphin 'foretell' and 分 fēn 'divide'bǔfēnTransliteration. Formerly known as 㗊 léi, which depicts the porphin ring system pictographically. 卟 is also pronounced , meaning 'divination' or 'to consider'. 吩 is also used to mean 'to instruct, command'.
alcoholxiǎng 'enjoy'chúnNot newly coined, original meaning 'rich wine'
噠嗪/哒嗪 pyridazine達/达 'arrive at' and 秦 qín 'Qin Dynasty'dāqínTransliteration.
噁唑/𫫇唑 oxazole惡/恶 è 'evil' and 坐 zuò 'sit'èzuòTransliteration.
acenaphtheneè 'hardship'èEuropean pronunciation
anthraceneēn 'favor'ēnEuropean pronunciation. 蒽 is also used as a name of a grass.
phenanthrenefēi 'not'fēiEuropean pronunciation. 菲 is also used to mean 'fragrant'. This character is also read as fěi to mean 'poor'.
酚 (also 苯酚) phenolfēn 'divide'fēn (běnfēn)European pronunciation
碸/砜 sulfone風/风 fēng 'the wind'fēngEuropean pronunciation (亞碸/亚砜 yàfēng [lit. minor sulfone], is used for sulfoxide)
呋喃 furan 'husband' and 南 nán 'south'fūnánTransliteration. 呋 is also a variant of 趺 ('back of the foot' or 'to sit cross-legged'). 喃 is also used to mean 'chattering' or 'to mumble'
呋咱 furazan 'husband' and 自 'self'fūzánTransliteration. 咱 is also used to mean 'we'.
酐 (organic or inorganic) anhydridegān 'dry'gānFrom (simplified) 干 gān 'dry'. This character is also used to mean 'bitter wine'.
glycosidegān 'sweet'gānFrom 甘 gān 'sweet'. Formerly known as 甙 dài, composed of 弋 from 代 dài 'substitute' and 甘 gān 'sweet'. 苷 is also used to mean 'licorice'.
guanidineguā 'melon'guāEuropean pronunciation. This character is also pronounced as to mean 'large abdomen' or 'stoutness'.
hydroxylaminehài '9-11 pm'hǎiEuropean pronunciation. This character is also pronounced as gāi to mean 'the flesh where hair grows on the big toe' or 'prepare'; it is also pronounced gǎi to mean 'cheek'.
sulfonyl黃/黄 huáng 'yellow'huángFrom 硫磺 liúhuáng 'sulfur'; e.g., 磺胺 huáng'àn (Taiwan huáng'ān) is sulfonamide
nitrileqīng 'blue', 'green'jīngFrom cyanogen, 氰 qíng (Taiwan qīng), itself derived from 青 qīng, blue/green/cyan, cf. Prussian blue. It is also used to mean 'pure meat'.
hydrazinejǐng 'a well'jǐngEuropean pronunciation
isonitrile 'stop','check'From older nomenclature carbylamine (Also known as 異腈/异腈 yìjīng [lit. different nitrile])
蒈 caranejiē 'all'kǎiEuropean pronunciation
camphanekǎn 'threshold'kǎnEuropean pronunciation
喹啉 quinolinekuí 'stride' and 林 lín 'forest'kuílínTransliteration. 啉 is also pronounced as lán to mean 'greed', 'drink a round of wine', 'finish drinking' or 'piercing noise'; it is also pronounced as lìn or làn to mean 'stupid'.
quinonekūn 'elder brother'kūnEuropean pronunciation
phosphinelínlìnFrom 磷 lín 'phosphorus', itself from 粦 lín 'will-o'-the-wisp' (Phosphonium is 鏻 lǐn, in analogy to ammonium). Pronounced as lín in Taiwan. 膦 is also pronounced as liǎn to mean 'lack of strength'.
ether 'bewilder'From 迷 'confusion', from anesthetic properties of diethyl ether. This character is also used to mean 'drunk'.
mancude màn 'graceful' màn European pronunciation. The term mancude derives from maximum number of noncumulative double bonds. For example, a 7-membered mancude ring system has three double bonds in it (e.g. azepine, oxepine, ...).
amidine 'rice'European pronunciation
咪唑 imidazole 'rice' and 坐 zuò 'sit'mǐzuòTransliteration. 咪 is also pronounced as , used as onomatopoeia for cats or used to describe the appearance of a smile.
嘧啶 pyrimidine 'dense' and 定 dìng 'stability'mìdìngTransliteration
naphthalenenài 'persevere'nàiEuropean pronunciation
urea尿 niào 'urine'niàoFrom 尿 niào 'urine'
薴/苧 limonene寧/宁 níng 'peaceful'níngFrom 檸檬/柠檬 níngméng 'lemon'. 薴 is also used to mean 'messy'.
哌啶 piperidine𠂢 pài and 定 dìng 'stability'pàidìngTransliteration
哌嗪 piperazine𠂢 pài and 秦 qín 'Qin Dynasty'pàiqínTransliteration
pinenepài 'assign'pàiEuropean pronunciation
picene 'equal'European pronunciation
嘌呤 purinepiào 'ticket' and 令 lìng 'make'piàolìngTransliteration. Pronounced as piāolíng in Taiwan. 嘌 is also pronounced as piāo to mean 'passing swiftly' or 'speak'. 呤 is also pronounced as líng to mean 'speak with a soft voice'.
羥/羟 hydroxylyáng 'sheep' and 巠/𢀖 jīngqiǎngFrom fusion of the sounds of 氧 yǎng 'oxygen' and 氫/氢 qīng 'hydrogen'. This character is also pronounced qiān or kēng to mean 'a type of sheep'.
巰/巯 sulfhydryl巠/𢀖 jīng and 硫 liú 'sulfur'qiúFrom fusion of the sounds of 氫/氢 qīng 'hydrogen' and 硫 liú 'sulfur' (Sulfonium is 鋶/锍 liǔ, in analogy with ammonium)
aldehydequánquánFrom 荃 quán, a type of fragrant grass, referring to the fragrance of many aldehydes. 醛 is also pronounced as chuò to mean 'change in the flavour of wine' or 'pickled vegetables'.
alkyneguǎiquēFrom 缺 quē 'deficient', referring to its unsaturation, cf. names for alkanes and alkenes. Pronounced as jué in Taiwan. This character is also pronounced as guì, which is a surname or means 'the appearance of smoke'.
osazoneshā 'kill'European pronunciation
噻唑 thiazolesāi 'to stop up' and 坐 zuò 'sit'sāizuòEuropean pronunciation
arsineshēn 'explain'shènFrom 砷 shēn 'arsenic' (Arsonium is 鉮 shěn, in analogy with ammonium). Pronounced as shēn in Taiwan. This character is also pronounced as shēn to mean 'the flesh of the back'.
酸 (organic or inorganic) acid夋, qūnsuānNot newly coined, also means 'sour'
carboxyln.a.suōCharacter construction is based on combination of 氧 yǎng 'oxygen' and 酸 suān 'acid', pronunciation from European pronunciation. This character is also pronounced as zuī to mean 'woollen knitwear'.
peptidetài 'excessively'tàiEuropean pronunciation
phthaleintài 'excessively'tàiEuropean pronunciation
carbonylyáng 'sheep' and 炭 tàn 'charcoal'tāngFrom fusion of the sounds of 氧 yǎng 'oxygen' and 碳 tàn 'carbon'. Pronounced as tàn in Taiwan.
terpenetiè 'obedient'tiēEuropean pronunciation
烴/烃 hydrocarbon巠/𢀖 jīngtīngFrom fusion of the sounds of 碳 tàn 'carbon' and 氫/氢 qīng 'hydrogen'. The character is also read jǐng to mean 'warm', 'burnt smell' or 'the appearance of burning'.
ketonetóng 'same'tóngEuropean pronunciation. The character is also pronounced dòng to mean 'bad wine'.
alkanewán 'complete'wánFrom 完 wán 'complete', referring to its saturation, cf. names for alkenes and alkynes. The character is also used to mean 'fire'.
鎓/𬭩 oniumwēng 'old man'wēngEuropean pronunciation. Used in cases when a specific 'onium' character is unavailable or uncommon, e.g., 氧鎓/氧𬭩 yǎngwēng for 'oxonium'. The character is also used to mean 'spade'.
oxime 'in, on, at'European pronunciation. Formerly known as 胜 shēng, which is also an old variant of 腥 xīng 'rank, strong-smelling', as well as the simplified character for 勝 shèng/shēng 'victory' or 'excel'. Note that 亏 is also the unrelated simplified character for 虧 kuī 'deficit', but in this context, it is the archaic variant character for 于 'in, on, at'.
fluorene 'do not'European pronunciation. This character is also a name for an edible wild plant; it can also be pronounced to mean 'dimly' or 'suddenly'.
alkene 'infrequent'From 希 'sparse', referring to its unsaturation, cf. names for alkanes and alkynes. It can also mean 'the colour of fire'.
酰 (organic or inorganic) acylxiān 'in front'xiānFrom 先 xiān 'earlier [i.e. precursor]', referring to its derivation from acids. Formerly known as 醯 , which also means 'acid, vinegar'.
吲哚 indoleyǐn 'attract' and 朵 duǒyǐnduǒTransliteration
indeneyìn 'impression'yìnEuropean pronunciation. This character is also a name of a grass.
steroidzāi 'steroid'zāiPictographic in origin, referring to the three side-chains (found in cholesterol) and four rings found in all steroids. The character is a variant of 災/灾 zāi 'calamity'; it is also pronounced to mean 'an ancient pottery used for containing wine'.
esterzhǐ 'purpose'zhǐFrom 脂 zhī 'lipid', referring to the ester linkages in glycerides. Formerly known as 𨤎 yán.
tropyliumzhuó 'eminent'zhuóEuropean pronunciation
hydrazonezōng 'faction'zōngEuropean pronunciation

Other aspects and examples

In the CCS system, carbon chain lengths are denoted by celestial stems (甲 jiǎ, 乙 , 丙 bǐng, 丁 dīng, 戊 , 己 , 庚 gēng, 辛 xīn, 壬 rén, 癸 guǐ), characters used since the Shang Dynasty (16th-11th centuries BCE) for naming days (and later, to name years). For example, hexane is 己烷 jǐwán, since 己 is the sixth celestial stem. Longer carbon chains are specified by number followed by '碳' tàn 'carbon'. For example, 1-hexadecene is 1-十六碳烯 (read as [1, ] [-, wèi] [十六, shíliù, '16'] [碳, tàn] [烯, ]), where the hyphen is read as 位 (wèi, 'position').

For a more complex example, consider 3-buten-1-ol. Its Chinese name is 3-丁烯-1-醇 (read as [3, sān] [-, wèi] [丁, dīng] [烯, ] [1, ] [-, wèi] [醇, chún]).

The descriptors for degree of substitution, primary, secondary, tertiary, and quaternary, are translated as 伯 (),仲 (zhòng),叔 (shū),季 (), which refer to the first, second, third, and fourth male siblings in a family. For instance, tert-butyllithium is translated as 叔丁基锂 ([叔, shū, 'tert'], [丁, dīng, 'but-'], [基, , 'yl'], [锂, , 'lithium']). Other commonly used isomeric descriptors normal-, iso-, and neo- are translated as 正 (zhèng, 'proper'), 异 (, 'different'), and 新 (xīn, 'new'), respectively.

The numerical prefix bis- is translated as 双 (shuāng, 'double'), while larger multiplicities are simply given by the Chinese word for the number (e.g., 四 (, 'four') for tetrakis-). For example, tetrakis(triphenylphosphine)palladium is rendered 四(三苯基膦)钯, in which 三苯基膦 is triphenylphosphine and 钯 is palladium. The prefix bi- (for joining of ring systems) is translated as 联 (lián, 'join', 'couple'), as in 联苯 for biphenyl.

The stereochemical descriptors cis- and trans- are translated as 顺 (shùn, 'along') and 反 (fǎn, 'against'). The relational prefixes ortho-, meta-, and para- are translated as 邻 (lín, 'neighboring'), 间 (jiàn, 'between'), and 对 (duì, 'opposing'), respectively.

The structural modification descriptors nor- and homo- are translated as 降 (jiàng, 'lowered') and 高 (gāo, 'high'). For example, norbornene is translated as 降冰片烯, in which the trivial name (冰片) for bornyl [literally, camphor] is used.

The common unsaturated groups allyl and propargyl are translated as 烯丙(基) (xībǐng(jī), 'alkene-prop-(yl)') and 炔丙(基) (qūebǐng(jī), 'alkyne-prop-(yl)'). Thus, using 高 for homo- and 烯丙 for allyl, 3-buten-1-ol is also called 高烯丙醇 (i.e., homoallyl alcohol) in Chinese via semisystematic nomenclature.

The Chinese Wikipedia page may be consulted for further details.

See also

References

  1. Actually, there have existed two organizations with that name since 1950, as a consequence of the inconclusive resolution of the Chinese Civil War: one based in Beijing and the other based in Taipei. The organization based in Taipei has changed its English name to Chemical Society Located in Taipei while retaining its Chinese name. Besides the usage of simplified vs. traditional components for characters and slight differences in the rules for heterocyclic nomenclature, the rules adopted by the two organizations do not differ significantly.
This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.