植醇

Phytol
	IUPAC名; (2E,7R,11R)-3,7,11,15-; tetramethyl-2-hexadecen-1-ol
識別
CAS號	7541-49-3
PubChem	5280435
ChemSpider	4444094
SMILES	C[C@@H](CCC[C@@H](C)CCC/C(=C/CO)/C)CCCC(C)C;
InChI	1/C20H40O/c1-17(2)9-6-10-18(3)11-7-12-19(4)13-8-14-20(5)15-16-21/h15,17-19,21H,6-14,16H2,1-5H3/b20-15+/t18-,19-/m1/s1;
InChIKey	BOTWFXYSPFMFNR-PYDDKJGSBV
ChEBI	17327
性質
化學式	C20H40O
摩爾質量	296.53 g·mol−1
密度	0.850 g cm−3
沸點	203-204 °C （10 mmHg）
	若非註明，所有數據均出自標準狀態（25 ℃，100 kPa）下。

植醇（Phytol）是一種鏈狀的二萜醇，分子式C
20H
40O，用於維他命E和維他命K1的合成前體。^[1]^[2]植醇是葉綠素分子側鏈結構的組成部分。反芻動物的消化道中，葉綠素分解的游離植醇被動物吸收，轉化為植烷酸儲存在脂肪中。^[3]植醇在鯊魚肝臟中轉化為姥鮫烷。

人類病理學

有一種名為雷弗素姆病（英語：Refsum disease）的常染色體隱性遺傳病，患者體內植烷酸大量積累，導致多發性周圍神經病變、小腦共濟失調（英語：cerebellar ataxia）、視網膜色素變性、嗅覺缺失（英語：anosmia）和耳聾。^[4]儘管人體不能通過降解葉綠素獲取植醇，但能將游離植醇轉化為植烷酸。因此，雷弗素姆病患者必須嚴格控制植烷酸及游離植醇的攝取量。^[5]有研究系統測定了各種食材中植醇和植烷酸含量，發現食物中游離植醇含量一般不及該病患者需要控制飲食的濃度；植物及植物油中不含植烷酸，而反芻類動物和魚類的脂肪含有一定比例的植烷酸。^[6]

自然界

有研究稱漆樹跳甲（英語：Blepharida rhois）等昆蟲使用葉綠醇及其代謝產物（例如植烷酸）作為防止自己被捕食的化學威懾劑。^[7]這些化合物攝取自它的宿主植物。

間接的證據已經證明大型類人猿在植物的後腸發酵過程中可獲得數量可觀的植烷酸，這點與人類不同。^[8]^[9]

應用

地球化學生物標誌物

植醇可能是生物圈中最豐富的鏈狀萜類。植醇及其代謝產物可用作水生環境的生化示蹤劑。^[10]

商業應用

日化行業中，植醇用於化妝品、洗髮水、廁所肥皂、家用清潔劑和洗滌劑。^[11]世界年消耗量約0.1–1.0噸。^[12]

參考資料

^ Netscher, Thomas. Synthesis of Vitamin E. Litwack, Gerald (編). Vitamin E. Vitamins & Hormones 76. 2007: 155–202. ISBN 978-0-12-373592-8. doi:10.1016/S0083-6729(07)76007-7.
^ Daines, Alison; Payne, Richard; Humphries, Mark; Abell, Andrew. The Synthesis of Naturally Occurring Vitamin K and Vitamin K Analogues. Current Organic Chemistry. 2003, 7 (16): 1625–34. doi:10.2174/1385272033486279.
^ Van Den Brink, D. M.; Wanders, R. J. A. Phytanic acid: Production from phytol, its breakdown and role in human disease. Cellular and Molecular Life Sciences. 2006, 63 (15): 1752–65. PMID 16799769. doi:10.1007/s00018-005-5463-y.
^ Wierzbicki, A.S. Peroxisomal disorders affecting phytanic acid α-oxidation: A review. Biochemical Society Transactions. 2007, 35 (5): 881–6. PMID 17956237. doi:10.1042/BST0350881.
^ Komen, J.C.; Wanders, R.J.A. Peroxisomes, Refsum's disease and the α- and ω-oxidation of phytanic acid. Biochemical Society Transactions. 2007, 35 (5): 865–9. PMID 17956234. doi:10.1042/BST0350865.
^ Brown, P. June; Mei, Guam; Gibberd, F. B.; Burston, D.; Mayne, P. D.; McClinchy, Jane E.; Sidey, Margaret. Diet and Refsum's disease. The determination of phytanic acid and phytol in certain foods and the application of this knowledge to the choice of suitable convenience foods for patients with Refsum's disease. Journal of Human Nutrition and Dietetics. 1993, 6 (4): 295–305. doi:10.1111/j.1365-277X.1993.tb00375.x.
^ Vencl, Fredric V.; Morton, Timothy C. The shield defense of the sumac flea beetle, Blepharida rhois (Chrysomelidae: Alticinae). Chemoecology. 1998, 8 (1): 25–32. doi:10.1007/PL00001800.
^ Watkins, Paul A; Moser, Ann B; Toomer, Cicely B; Steinberg, Steven J; Moser, Hugo W; Karaman, Mazen W; Ramaswamy, Krishna; Siegmund, Kimberly D; Lee, D Rick; Ely, John J; Ryder, Oliver A; Hacia, Joseph G. Identification of differences in human and great ape phytanic acid metabolism that could influence gene expression profiles and physiological functions. BMC Physiology. 2010, 10: 19. PMC 2964658  . PMID 20932325. doi:10.1186/1472-6793-10-19.
^ Moser, Ann B; Hey, Jody; Dranchak, Patricia K; Karaman, Mazen W; Zhao, Junsong; Cox, Laura A; Ryder, Oliver A; Hacia, Joseph G. Diverse captive non-human primates with phytanic acid-deficient diets rich in plant products have substantial phytanic acid levels in their red blood cells. Lipids in Health and Disease. 2013, 12: 10. PMC 3571895  . PMID 23379307. doi:10.1186/1476-511X-12-10.
^ Rontani, Jean-François; Volkman, John K. Phytol degradation products as biogeochemical tracers in aquatic environments. Organic Geochemistry. 2003, 34 (1): 1–35. doi:10.1016/S0146-6380(02)00185-7.
^ McGinty, D.; Letizia, C.S.; Api, A.M. Fragrance material review on phytol. Food and Chemical Toxicology. 2010, 48: S59–63. PMID 20141879. doi:10.1016/j.fct.2009.11.012.
^ IFRA (International Fragrance Association（英語：International Fragrance Association）), 2004. Use Level Survey, August 2004.

[1] Netscher, Thomas. Synthesis of Vitamin E. Litwack, Gerald (編). Vitamin E. Vitamins & Hormones 76. 2007: 155–202. ISBN 978-0-12-373592-8. doi:10.1016/S0083-6729(07)76007-7.

[2] Daines, Alison; Payne, Richard; Humphries, Mark; Abell, Andrew. The Synthesis of Naturally Occurring Vitamin K and Vitamin K Analogues. Current Organic Chemistry. 2003, 7 (16): 1625–34. doi:10.2174/1385272033486279.

[pmid16799769-3] Van Den Brink, D. M.; Wanders, R. J. A. Phytanic acid: Production from phytol, its breakdown and role in human disease. Cellular and Molecular Life Sciences. 2006, 63 (15): 1752–65. PMID 16799769. doi:10.1007/s00018-005-5463-y.

[pmid17956237-4] Wierzbicki, A.S. Peroxisomal disorders affecting phytanic acid α-oxidation: A review. Biochemical Society Transactions. 2007, 35 (5): 881–6. PMID 17956237. doi:10.1042/BST0350881.

[5] Komen, J.C.; Wanders, R.J.A. Peroxisomes, Refsum's disease and the α- and ω-oxidation of phytanic acid. Biochemical Society Transactions. 2007, 35 (5): 865–9. PMID 17956234. doi:10.1042/BST0350865.

[6] Brown, P. June; Mei, Guam; Gibberd, F. B.; Burston, D.; Mayne, P. D.; McClinchy, Jane E.; Sidey, Margaret. Diet and Refsum's disease. The determination of phytanic acid and phytol in certain foods and the application of this knowledge to the choice of suitable convenience foods for patients with Refsum's disease. Journal of Human Nutrition and Dietetics. 1993, 6 (4): 295–305. doi:10.1111/j.1365-277X.1993.tb00375.x.

[7] Vencl, Fredric V.; Morton, Timothy C. The shield defense of the sumac flea beetle, Blepharida rhois (Chrysomelidae: Alticinae). Chemoecology. 1998, 8 (1): 25–32. doi:10.1007/PL00001800.

[pmid20932325-8] Watkins, Paul A; Moser, Ann B; Toomer, Cicely B; Steinberg, Steven J; Moser, Hugo W; Karaman, Mazen W; Ramaswamy, Krishna; Siegmund, Kimberly D; Lee, D Rick; Ely, John J; Ryder, Oliver A; Hacia, Joseph G. Identification of differences in human and great ape phytanic acid metabolism that could influence gene expression profiles and physiological functions. BMC Physiology. 2010, 10: 19. PMC 2964658  . PMID 20932325. doi:10.1186/1472-6793-10-19.

[pmid23379307-9] Moser, Ann B; Hey, Jody; Dranchak, Patricia K; Karaman, Mazen W; Zhao, Junsong; Cox, Laura A; Ryder, Oliver A; Hacia, Joseph G. Diverse captive non-human primates with phytanic acid-deficient diets rich in plant products have substantial phytanic acid levels in their red blood cells. Lipids in Health and Disease. 2013, 12: 10. PMC 3571895  . PMID 23379307. doi:10.1186/1476-511X-12-10.

[10] Rontani, Jean-François; Volkman, John K. Phytol degradation products as biogeochemical tracers in aquatic environments. Organic Geochemistry. 2003, 34 (1): 1–35. doi:10.1016/S0146-6380(02)00185-7.

[11] McGinty, D.; Letizia, C.S.; Api, A.M. Fragrance material review on phytol. Food and Chemical Toxicology. 2010, 48: S59–63. PMID 20141879. doi:10.1016/j.fct.2009.11.012.

[12] IFRA (International Fragrance Association（英語：International Fragrance Association）), 2004. Use Level Survey, August 2004.

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Phytol

IUPAC名 (2E,7R,11R)-3,7,11,15- tetramethyl-2-hexadecen-1-ol
識別
CAS號	7541-49-3 ^Y
PubChem	5280435
ChemSpider	4444094
SMILES	C[C@@H](CCC[C@@H](C)CCC/C(=C/CO)/C)CCCC(C)C
InChI	1/C20H40O/c1-17(2)9-6-10-18(3)11-7-12-19(4)13-8-14-20(5)15-16-21/h15,17-19,21H,6-14,16H2,1-5H3/b20-15+/t18-,19-/m1/s1
InChIKey	BOTWFXYSPFMFNR-PYDDKJGSBV
ChEBI	17327
性質
化學式	C₂₀H₄₀O
摩爾質量	296.53 g·mol⁻¹
密度	0.850 g cm⁻³
沸點	203-204 °C （10 mmHg）
若非註明，所有數據均出自標準狀態（25 ℃，100 kPa）下。