Organic nomenclature in Chinese
The Chinese Chemical Society[lower-alpha 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.
| Character | Phonetic | Pronunciation | Origin/Notes |
|---|---|---|---|
| 胺 amine | 安 ān 'peace' | àn | From 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)'. |
| 薁 azulene | 奥 ào 'mysterious' | ào | European pronunciation. This character is also pronounced yù, meaning 'wild grapes'. |
| 苯 benzene or phenyl | 本 běn 'this','root' | běn | European pronunciation. This character is also used to mean 'the appearance of grass growing'. |
| 吡啶 pyridine | 比 bǐ 'compare' and 定 dìng 'stability' | bǐdìng | Transliteration. 吡 is also used to mean 'slander' or 'compare'; when it is pronounced bì, it is bird onomatopoeia. |
| 吡咯 pyrrole | 比 bǐ 'compare' and 各 gè 'each' | bǐluò | Transliteration. See note for 吡啶 for other usages for 吡. 咯 is also pronounced gē or gé, meaning 'cackle', 'cluck', 'this', or 'pickled mustard'; it is also pronounced kǎ (luò in Taiwan), meaning 'to cough up'; it is also pronounced lo, used as an end particle. |
| 吡喃 pyran | 比 bǐ 'compare' and 南 nán 'south' | bǐnán | Transliteration. In general, 喃 is used to transliterate '-ran'. |
| 吡喃鎓 pyrylium | 比 bǐ 'compare', 南 nán 'south', and 翁 wēng 'old man' | bǐnánwēng | Combination of transliteration for 'pyran' and suffix for 'onium'. |
| 苄 benzyl | 卞 biàn 'hurried' | biàn | European pronunciation |
| 卟吩 porphin | 卜 bǔ 'foretell' and 分 fēn 'divide' | bǔfēn | Transliteration. Formerly known as 㗊 léi, which depicts the porphin ring system pictographically. 卟 is also pronounced jī, meaning 'divination' or 'to consider'. 吩 is also used to mean 'to instruct, command'. |
| 醇 alcohol | 享 xiǎng 'enjoy' | chún | Not newly coined, original meaning 'rich wine' |
| 噠嗪/哒嗪 pyridazine | 達/达 dá 'arrive at' and 秦 qín 'Qin Dynasty' | dāqín | Transliteration. |
| 噁唑/𫫇唑 oxazole | 惡/恶 è 'evil' and 坐 zuò 'sit' | èzuò | Transliteration. |
| 苊 acenaphthene | 厄 è 'hardship' | è | European pronunciation |
| 蒽 anthracene | 恩 ēn 'favor' | ēn | European pronunciation. 蒽 is also used as a name of a grass. |
| 菲 phenanthrene | 非 fēi 'not' | fēi | European pronunciation. 菲 is also used to mean 'fragrant'. This character is also read as fěi to mean 'poor'. |
| 酚 (also 苯酚) phenol | 分 fēn 'divide' | fēn (běnfēn) | European pronunciation |
| 碸/砜 sulfone | 風/风 fēng 'the wind' | fēng | European pronunciation (亞碸/亚砜 yàfēng [lit. minor sulfone], is used for sulfoxide) |
| 呋喃 furan | 夫 fū 'husband' and 南 nán 'south' | fūnán | Transliteration. 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 | 夫 fū 'husband' and 自 zì 'self' | fūzán | Transliteration. 咱 is also used to mean 'we'. |
| 酐 (organic or inorganic) anhydride | 干 gān 'dry' | gān | From (simplified) 干 gān 'dry'. This character is also used to mean 'bitter wine'. |
| 苷 glycoside | 甘 gān 'sweet' | gān | From 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'. |
| 胍 guanidine | 瓜 guā 'melon' | guā | European pronunciation. This character is also pronounced as gū to mean 'large abdomen' or 'stoutness'. |
| 胲 hydroxylamine | 亥 hài '9-11 pm' | hǎi | European 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'. |
| 磺 sulfonyl | 黃/黄 huáng 'yellow' | huáng | From 硫磺 liúhuáng 'sulfur'; e.g., 磺胺 huáng'àn (Taiwan huáng'ān) is sulfonamide |
| 腈 nitrile | 青 qīng 'blue', 'green' | jīng | From cyanogen, 氰 qíng (Taiwan qīng), itself derived from 青 qīng, blue/green/cyan, cf. Prussian blue. It is also used to mean 'pure meat'. |
| 肼 hydrazine | 井 jǐng 'a well' | jǐng | European pronunciation |
| 胩 isonitrile | 卡 kǎ 'stop','check' | kǎ | From older nomenclature carbylamine (Also known as 異腈/异腈 yìjīng [lit. different nitrile]) |
| 蒈 carane | 皆 jiē 'all' | kǎi | European pronunciation |
| 莰 camphane | 坎 kǎn 'threshold' | kǎn | European pronunciation |
| 喹啉 quinoline | 奎 kuí 'stride' and 林 lín 'forest' | kuílín | Transliteration. 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'. |
| 醌 quinone | 昆 kūn 'elder brother' | kūn | European pronunciation |
| 膦 phosphine | 粦 lín | lìn | From 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'. |
| 醚 ether | 迷 mí 'bewilder' | mí | From 迷 mí 'confusion', from anesthetic properties of diethyl ether. This character is also used to mean 'drunk'. |
| 熳 mancude | 曼 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, ...). |
| 脒 amidine | 米 mǐ 'rice' | mǐ | European pronunciation |
| 咪唑 imidazole | 米 mǐ 'rice' and 坐 zuò 'sit' | mǐzuò | Transliteration. 咪 is also pronounced as mī, used as onomatopoeia for cats or used to describe the appearance of a smile. |
| 嘧啶 pyrimidine | 密 mì 'dense' and 定 dìng 'stability' | mìdìng | Transliteration |
| 萘 naphthalene | 奈 nài 'persevere' | nài | European pronunciation |
| 脲 urea | 尿 niào 'urine' | niào | From 尿 niào 'urine' |
| 薴/苧 limonene | 寧/宁 níng 'peaceful' | níng | From 檸檬/柠檬 níngméng 'lemon'. 薴 is also used to mean 'messy'. |
| 哌啶 piperidine | 𠂢 pài and 定 dìng 'stability' | pàidìng | Transliteration |
| 哌嗪 piperazine | 𠂢 pài and 秦 qín 'Qin Dynasty' | pàiqín | Transliteration |
| 蒎 pinene | 派 pài 'assign' | pài | European pronunciation |
| 苉 picene | 匹 pǐ 'equal' | pǐ | European pronunciation |
| 嘌呤 purine | 票 piào 'ticket' and 令 lìng 'make' | piàolìng | Transliteration. 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 hydroxyl | 羊 yáng 'sheep' and 巠/𢀖 jīng | qiǎng | From 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' | qiú | From fusion of the sounds of 氫/氢 qīng 'hydrogen' and 硫 liú 'sulfur' (Sulfonium is 鋶/锍 liǔ, in analogy with ammonium) |
| 醛 aldehyde | 荃 quán | quán | From 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'. |
| 炔 alkyne | 夬 guǎi | quē | From 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'. |
| 脎 osazone | 杀 shā 'kill' | sà | European pronunciation |
| 噻唑 thiazole | 塞 sāi 'to stop up' and 坐 zuò 'sit' | sāizuò | European pronunciation |
| 胂 arsine | 申 shēn 'explain' | shèn | From 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, qūn | suān | Not newly coined, also means 'sour' |
| 羧 carboxyl | n.a. | suō | Character 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'. |
| 肽 peptide | 太 tài 'excessively' | tài | European pronunciation |
| 酞 phthalein | 太 tài 'excessively' | tài | European pronunciation |
| 羰 carbonyl | 羊 yáng 'sheep' and 炭 tàn 'charcoal' | tāng | From fusion of the sounds of 氧 yǎng 'oxygen' and 碳 tàn 'carbon'. Pronounced as tàn in Taiwan. |
| 萜 terpene | 帖 tiè 'obedient' | tiē | European pronunciation |
| 烴/烃 hydrocarbon | 巠/𢀖 jīng | tīng | From 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'. |
| 酮 ketone | 同 tóng 'same' | tóng | European pronunciation. The character is also pronounced dòng to mean 'bad wine'.
Warning: Verbally, 酮 ('ketone') and 铜 ('copper') are both pronounced tóng and are indistinguishable. In modern times, new chemical terminology is chosen to avoid conflicts like this. |
| 烷 alkane | 完 wán 'complete' | wán | From 完 wán 'complete', referring to its saturation, cf. names for alkenes and alkynes. The character is also used to mean 'fire'. |
| 鎓/𬭩 onium | 翁 wēng 'old man' | wēng | European 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'. |
| 肟 oxime | 亏 yú 'in, on, at' | wò | 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 yú 'in, on, at'. |
| 芴 fluorene | 勿 wù 'do not' | wù | European pronunciation. This character is also a name for an edible wild plant; it can also be pronounced hū to mean 'dimly' or 'suddenly'. |
| 烯 alkene | 希 xī 'infrequent' | xī | From 希 xī 'sparse', referring to its unsaturation, cf. names for alkanes and alkynes. It can also mean 'the colour of fire'. |
| 酰 (organic or inorganic) acyl | 先 xiān 'in front' | xiān | From 先 xiān 'earlier [i.e. precursor]', referring to its derivation from acids. Formerly known as 醯 xī, which also means 'acid, vinegar'. |
| 𨦡 oxonium | 羊 yáng 'goat; sheep' | yáng | From oxygen, 氧 yǎng |
| 吲哚 indole | 引 yǐn 'attract' and 朵 duǒ | yǐnduǒ | Transliteration |
| 茚 indene | 印 yìn 'impression' | yìn | European pronunciation. This character is also a name of a grass. |
| 甾 steroid | 甾 zāi 'steroid' | zāi | Pictographic 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 zī to mean 'an ancient pottery used for containing wine'. |
| 酯 ester | 旨 zhǐ 'purpose' | zhǐ | From 脂 zhī 'lipid', referring to the ester linkages in glycerides. Formerly known as 𨤎 yán. |
| 䓬 tropylium | 卓 zhuó 'eminent' | zhuó | European pronunciation |
| 腙 hydrazone | 宗 zōng 'faction' | zōng | European pronunciation |
Other aspects and examples
In the CCS system, carbon chain lengths are denoted by celestial stems (甲 jiǎ, 乙 yǐ, 丙 bǐng, 丁 dīng, 戊 wù, 己 jǐ, 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 jǐ 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, yī] [-, wèi] [十六, shíliù, '16'] [碳, tàn] [烯, xī]), 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, xī] [1, yī] [-, wèi] [醇, chún]).
The descriptors for degree of substitution, primary, secondary, tertiary, and quaternary, are translated as 伯 (bó), 仲 (zhòng), 叔 (shū), 季 (jì), 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, jī, 'yl'], [锂, lǐ, 'lithium']). Other commonly used isomeric descriptors normal-, iso-, and neo- are translated as 正 (zhèng, 'proper'), 异 (yì, '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 (sì, '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 cyclo-, nor- and homo- are translated as 环 (huán, 'ring'), 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. When substitutive nomenclature is used for naming heterocycles, the suffix 杂 (zá, 'mixed') is used in the same way as '-a' in English (as in aza, thia, oxa, etc.). As an example, DABCO (1,4-diazabicylo[2.2.2]octane) is named 1,4-二氮杂二环［2.2.2］辛烷.
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.
Thermochemical terminology
Although not substances, the thermochemical concepts entropy and enthalpy were assigned Chinese characters based on similar considerations. The 'fire' radical, 火, is used as the semantic category. The character for entropy, 熵 (pinyin: shāng), is derived from 商 (pinyin: shāng), which means 'quotient' in this context. This recognizes the Clausius equation for the differential change in entropy as the differential heat absorbed divided by the temperature: dS = dQ/T. The character for enthalpy, 焓 (pinyin: hán), is derived from 含 (pinyin: hán), which means 'to contain.' This character phonetically approximates the first syllable of 'enthalpy', and recognizes the definition of enthalpy as heat content.
Notes
- 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.